THE MINISTRY OF HEALTH OF THE REPUBLIC OF
UZBEKISTAN
TASHKENT MEDICAL ACADEMY
"Approved"
Vice-Rector of Tashkent Medical
Academy prof. Teshaev O.R.
"___" ____________2013 Year
Department: BIOORGANIC AND BIOLOGICAL CHEMISTRY
Subject: BIOORGANIC CHEMISTRY
THE TECHNOLOGY OF TRAINING
ON THE LABORATORY LESSON
TOPIC:
THE REACTIONS OF NUCLEOPHILIC SUBSTITUTION SN OF
CARBOXYLIC ACIDS AND THEIR FUNCTIONAL DERIVATIVES
Methodical recommendations
Tashkent - 2013
Author: Turayeva G.I. – assistant, department of bioorganic and biological
chemistry TMA
Reviewers:
Alimkhodjaeva N.A. - associate professor, department
bioanorganic, bioorganic and biological chemistry TashPMI
Zaytseva O.A. – D.F. associate professor, department
pharmacologies ТMА
of
of
Considered and approved at a meeting of the DNC medical-biological disciplines
__________________ 2013 minute №
2
Topic: THE REACTIONS OF NUCLEOPHILIC SUBSTITUTION SN OF
CARBOXYLIC ACIDS AND THEIR FUNCTIONAL DERIVATIVES
1. Model of technology education
Duration of studies:
Number of students: 12-15 persons
135 minutes
Department of bioorganic and biological
Location of activities:
chemistry
1. Introduction
The structure of the training
session
2. The theoretical part
3. Independent work of the student
4. Experimental part
5. The analytical part 6. Conclusion
The aim of the study lessons: to acquaint students with individual representatives,
chemical properties and biological value of carboxylic acids and their functional
derivatives. To form practical skills of conducting a qualitative reaction on acetic acid,
high-molecular fatty acid and oxalic acid.
The student should know: Theory of chemical structure of organic compounds,
types of reactions, mechanisms of the reactions, the structure features of a carboxyl
group, characterizing properties and the biological significance of these compounds.
The student should be able to: carry out qualitative reaction on acetic acid, receive
high-molecular fatty acids in the form of calcium salts and open oxalic acid in the form
of calcium salts.
The pedagogical objectives:
The results of educational activity:
• To acquaint with the structure and Students:
properties of carboxyl group
• Aware of the structure and correctly write
• Examine the reactivity and the formula of carboxylic acids and their
reactionary centers carboxyl group
functional derivatives
• Study properties and structure of • Know the structure of the carboxyl group
carboxylic acids and their derivatives
• Know how to determine the reactivity and
• Examine the SN reaction of reaction centers of carboxylic acids and
carboxylic acids and their derivatives
their functional derivatives
• Examine the the reaction of the • Know how to carry out the reaction of the
esterification and to acquaint with the esterification
received product
• Correctly write the equations of the
• To study the reaction of hydrolysis of reactions of hydrolysis of esters and
esters and tioesters and explain their tioesters
biological value
• Know S reaction of amides and nitriles
N
• Examine the SN reaction of amides carboxylic acids
and nitriles carboxylic acids
• Know the reaction of carboxylic acids
 Show the reaction of carboxylic acids with hydrazides
3
with hydraes
 To acquaint with anhydrides of
carboxylic acids
 Show condensation reactions, carried
out with the help of acetylecoferment A
and their SN mechanism
 Show the reaction of receipt of halogen
anhydrides acids
 Explain the biological significance of
carboxylic acids and their functional
derivatives
The technique and methods of
training:
Forms of training:
Means of training:
Monitoring and evaluation
• Know the reaction of
anhydrides of carboxylic acids
obtaining
• Know the reaction of condensation,
carried
out
with
the
help
of
acetylecoferment A and their SN
mechanism

Know the value of these reactions in
medicine
Conversation, discussion, “Brainstorming”,
drafting of graphic organizers, the
decision of situational tasks and tests
Individual work, work together in small
groups
Training manuals, training materials,
presentation slides, handouts, methodical
development step-by-step implementation
experiments, Internet sites in the field of
chemistry.
Oral questioning, blitz-poll, situational
tasks, tests
2. Technological map of learning activities based on interactive teaching
method «Brainstorming»
Stages of
the Content of the activity
work and time
Teacher
Student
(135 minutes)
1-stage
1.1. Checks attendance
Listen, write
Introduction
1.2. Announces topic, purpose and expected
(5 minutes)
results.
Listen to
1.3. Acquaints with the plan and the
peculiarities of the training session.
To clarify, ask
1.4. Introduces the criteria of assessment of questions
knowledge and skills of students
2-stage
22.1. Checks the level of preparedness of
Answer questions
The
students, ask questions, get answers on the topic.
theoretical
2.2. Gives an explanation on unclear issues
Listen, ask
part
questions
(50 minutes)
2.3. Shows the video on the topic of chemical
Examine and
properties of carboxylic acids
make conclusions and
expand their
understanding of
4
3-stage
Independent
work (20
minutes)
4-stage.
Practical part
(30 minutes)
5-stage
Analytic part
(20 minutes)
6-stage. The
final part
(10 minutes)
properties of
carboxylic acids
2.4. Sets out the scenario of interactive
To clarify, ask
teaching «Brainstorming» (5.3) and divides the questions, and are
students into small groups (Appendix № 2).
divided into small
groups
2.5. Actuate activity of students on the basis
of technology of training «Brainstorming»:
Work in a group,
assesses the work of the groups (individual ask questions, and
participants), makes conclusions on mutual make a presentation,
estimation participants.
evaluate their own
and their mutual
2.6. Sums up the results of the theoretical activities.
part of the class.
Listen to voice their
opinion,
3.1. Verifies the implementation of
Discuss, Express
extracurricular (drawing up of textbooks, work their opinions, fulfill
with literature and etc.) and class (filling in the the tasks of the IWS
tables, graphic organizers, etc.) part of the self
study work
4.1. Gives students the instructions on the
Listening, asking
implementation of the practical part of the class
questions
4.2. Gives the assignment of students to
Carry out the
perform experiments
laboratory work, the
4.3. Check the results of practical work
results of the issue in
the notebook, make
conclusions, make a
presentation of the
5 5.1. Sets for the solution of situational tasks
Solve
the
and tests and evaluates
tasks,tests, ask vague
questions, discuss
6.1. Makes a conclusion on the subject,
focusing students on the importance of the work
on the follow-up and analyses the degree of
achievement of the exercise.
6.2. Assesses the knowledge of students on
the results of assimilation of the theory, practice
and independent work and announces
assessment.
6.3. Specifies the task to the next session,
shall announce the list of literature and websites
on the Internet
Listen to
Listen to
Listen to
Record
5
3. Motivation
Carboxylic acids and their functional derivatives are included in the composition
of a large number of metabolites and medicinal substance. For the study of the
participation of these compounds in the process of vital activity of an organism need
to know their structure and properties.
4. Interdisciplinary and intersubject connection
Mastering of the topic students is based on the initial level of knowledge on
organic and inorganic chemistry, biology, physics, mathematics, etc. The knowledge
received during this session will be needed when studying the processes of
metabolism in the course biochemistry, histology, normal and pathological
physiology, pharmacology, clinical pharmacology, and also in the development of
practical skills for working with the laboratory, and medicines.
5. The theoretical part
5.1. Control questions
1. Specify the reactionary centers connections to the carboxyl group, and then
name the factors influencing their reactivity.
2. Write a general mechanism of the reactions of nucleophilic substitution of
carboxylic acids and their functional derivatives.
3. Write the reaction of receipt of halogen anhydrides, amides, tioesters, esters and
anhydrides of carboxylic acids, explain the mechanism of reactions.
4. Write the reaction of hydrolysis of derivatives of carboxylic acids.
5. Explain the reaction of condensation of carboxylic acids.
6. Tell us about the biological significance of carboxylic acids and their functional
derivatives.
5.2. The workshop sessions
Reactivity of carboxylic acids
Compounds in which one or more hydrogen atoms are replaced by carboxyl group
– СООН called carboxylic acids. Depending on the nature of organic radical RСООН carboxylic acids can be aliphatic, aromatic and heterocyclic. Carboxylic acids
on the number of carboxyl groups are divided into one main, two main and
polycarboxylic. For example, acetic СН3СООН and benzoic С6Н5СООН one main
acid, malon СООН - CH2 - СООН and terephthalic СООН- С6Н4 - СООН two main
acid. There are also saturated or unsaturated carboxylic acids.
Carboxylic acids are relatively high acidity.
Due to the-M-effect increases the mobility of hydrogen hydroxyl group. Due to
the separation of a proton from the hydroxyl group is formed high-stability
carboxylate - ion, communications and the charges in which aligned:
6
The reactionary centers of carboxylic acids and their derivatives
The reactions of nucleophilic substitution are characteristic of carboxylic acids
and their functional derivatives. In addition to electrofille the main and the weak CHacid centres available in aldehydes and ketons in a molecule of carbon acids and their
functional derivatives is also associated with carbon atom of carbonyl group deputy X
(potential leaving the group, nucleofuge), the ability to go in the form of anion X AC
or conjugate acid HX
.
At the expense +I-effect of negatively charged oxygen atom at carbon atom in the
product accession there is a partial negative chargeд which facilitates the separation
of the outgoing group X.
On the mechanism of the reaction proceeds in the presence of strong enough
nucleophile Y and the good of the outgoing group X. Easy nucleophilic attack
depends on the value of effective positive charge of the carbonyl group. In functional
derivatives of carboxylic acids R-CO-X it increases with the-I-effect of a deputy X
and decreases with increasing its +M-effect. Electrofile carbonyl carbon atom is
reduced by +M-effect of the functional deputy X associated with the carbon atom of
carbonyl group. For this reason, the nucleophilic reactions of derivatives of carboxylic
acids are often essential acid catalysis - protronation of the oxygen atom of carbonyl
group leads to the appearance of the full of positive charge at carbon atomа which
facilitates the attack nucleofille.
7
Factors influencing on reactivity of carboxylic acids.
The reactions of nucleophilic substitution of SN carboxylic acids and their
functional derivatives.
Getting halogen anhydrides
Halides are the most active acilic reagents among derivatives of carboxylic acids.
So, atsetilecholoride easily hydrolyses in water (atsetilate water) with heat release and
the formation of acetic acid. Halides RCOHal receive action (PCl5, PCl3) or
tionil chloride (SOCl2) on acid.
Getting anhydrides. When replacing the hydrogen hydroxyl group of carboxylic
acids on the balance of carboxylic acids are formed anhydrides acids. In practice
anhydrides are as follows:
8
Acetic acid
Anhydrides easily hydrolysable by with the formation of acids:
There are still mixed anhydrides consisting of residues of organic and mineral
acids. These include atsetilenitrate СН3СООNO2 and atsetilefosfate. Atsetilefosfate,
substituted atsetilfosfate and substituted atsilfosfate play an important role in
biochemical processes of the organism:
Atsetilfosfate
Substituted atsetilfosfate
Substituted atsilfosfate
(R - balance adenosine nucleoside, R’ radical carboxylic acid).
Substituted atsilfosfates are metabolites, with participation of which in the body is
the transfer of acil residuumes for hydroxyl, tionyl and аmino groups of various
compounds.
Esters and tioesters. Interaction of carboxylic acids from alcohols, leading to the
formation of esters, i.e. the reaction of the esterification is the most important process
of transformation of carboxylic acids and their functional derivatives.
The esterification reaction in the absence of catalysts is very slow due to the
already the low capacity of carbonyl groups in carboxylic acids to be subjected to
nucleophilic attack due to the +M- effect of OH group reduction and positive charge
at carbon atom. However, in the presence of mineral acids (sulfuric, HCl) reaction
considerably speeded up.
9
The process of esterification is reversible. Below is the mechanism of this reaction.
Complex esters RCOOR' and complex tioesters RCOSR' - the most widespread in
the nature as derivatives of carboxylic acids. Many medicines contain in their
composition of the ester group.
Hydrolysis. Esters may be subjected to hydrolysis (in contrast to the reaction of
the esterification) in both acidic and alkaline environments.
Hydrolysis in the alkaline environment is irreversible and requires ekvimoleculare
number of alkali.
The following scheme of the mechanism is fair to alkaline hydrolysis not only
esters, but also tioesters, halogen anhydrides, anhydrides and carboxylic acid amides.
The cause of the irreversibility of hydrolysis in the alkaline environment is the
formation of a stable masomer atsilate-ion.
The most common representative of these substances in the body is acetyl
coenzyme A (coenzyme of acetylation) – tioester of acetic acid and coenzyme A.
Atsetilecoenzyme A in vivo serves as a carrier of acetyl groups on nucleofile
substrates.
10
For example, with the participation of acetile coenzyme A precedes transformation
of choline in acetilcholine.
Atsetilecofermente A receives the following way:
Amides of carboxylic acids. At the substitution of hydroxyl group carboxylic
acid on aminogroup NH2 form amides of carboxylic acids:
Amides of carboxylic acids have a weakly acidic and weakly basic property.
Including of the electron acceptor acilic balance in the molecule of ammonia, leads to
the appearance of diluted acidic properties. Under the influence of +M-effect amides
are weakly basic properties compared with amines. The basic properties of amides
acids are evident in the reactions of formation of salts with stronger acids:
Amide group СN found in many biologically important
 
О Н
Substances, such as peptides and proteins.
Nitriles of carboxylic acids. Nitriles of carboxylic acids are obtained by
dehydration of acid amides:
As well as under the action of cyanide of alkaline metals on haloidalkils:
RBr  KCN  KBr  RC  N
Hydration nitriles pass in an alkaline environment. It can be imagined as
nucleophilic addition of water to a polarized triple connection nitrile with the
11
formation of the interim iminol, which are further changes in amide.
Nitriles represent more weak bases than amides. They are deprived of their basic
properties.When restoring nitriles into the corresponding amines:
R – C  N + 2H2  R – CH2 – NH2
One of the most important representatives of nitriles is acetonitrile CH3-С N.
Condensation reactions. Condensation reactions, which are based on the
ability of a carbonyl compounds to join the carbonyl group of the same or another
carbonyl compounds are typical not only for aldehydes and ketones, but also for the
derivatives of carboxylic acids in particular esters and tioefireов. Such reactions are
of great biological importance. With their help in the body leads to the formation of
new relations of the carbon-carbon. Indispensable participants of reactions by type
альдольного accession in vivo are tioesters of carboxylic acids - derivative
coenzyme A. In tioesters, compared with the usual esters due to the effective
positive charge on carbonil carbon atom nucleophilic substitution in the atom is
easier. For the same reason α - hydrogen atoms in tioesters more mobile and more
active in the reactions of condensation.
Biological importance of carbon acids.
Formic acid НСООН is contained in the nettles and in separations of the ants, it
is irritating to the skinу can cause burns. In medicine 1.25% alcohol solution of
formic acid is used in the treatment of rheumatism.
Acetic acid is a product of acetic fermentation of sugars. In medicine is applied in
the form of salts. Potassium acetate СН3СООК - moderate diuretic agent; lead acetate
(СН3СОО)2РЬ • ЗН20 - astringent, is used for inflammatory diseases of the skin and
mucous membranes. Acetic acid is used for food preservation.
Succinic acid has an unpleasant smell, is contained in gone bust oil and
perspiration.
Isovaleric acid is in the roots of valerian; a member of validol, valerian tincture.
Has a calming effect.
Sodium benzoate C6H5COONa - expectorant and poorly Dezin-фицирующее
means.A large medical-biological importance is the derivative of carbonic acid urethanes, ureid - and guanid derivatives.
12
Urethanes - esters of carbomide acid H2NCOOR - have psychic effect. Some of
them are used in nervous and mental diseases, showing sedative action. In particular,
meprotane (meprobamat) is used as a tranquilizer.
5.3. Description of the method «Brainstorming»
- (brainstorming-a storm of the brain), the
Brainstorming
method of collective generation of
ideas solution of practical or scientific
problems.
-separate ideas from their evaluation and
The main idea of the method
analysis. The idea becomes a guide to
all the actions of the leading
questioning and to help participants to
give as much as possible of new ideas.
-express (generate) as much as possible
The rules of questioning
of their own ideas of its decision and
write on the boar.
Divides the participants into 3-4 groups
Teacher
and offers each mini-group problems
(Appendix № 2)
-encouraging
participants
(smile,
encourage phrases, interjections);
gently, but insistently prevent attempts to
criticize other people's statements;
-records every statement in an
unmodified form
- to overcome the psychological barrier in
communication and providing moral
assistance to the students the students
are asked unexpected and original quiz
questions
from
a
current
or
предидушей topics (Appendix № 1)
-to discuss and evaluate each the idea;
After questioning
-give the best ideas;
6. TASKS FOR INDEPENDENT WORK OF STUDENTS
6. 1. Presentation of independent work of a student, who has received a task on
this topic: Annex № 3
6.2 Auxiliary means of training: graphic organizers
Graphic organizer: «Lotus Flower» - figure: the Means of solving problems.
Embodies the image of a lotus flower. It is based on the nine large squares, each of
which is formed of 9 squares. Develops and activates the system, creative, analytical
thinking.
The rules of drawing up of the “Lotus Flower”:
13
When solving this type of graphic organizer students write in the centre of the central
square of the basic idea. The concept of its decision recorded in the other eight
squares, located around the central.
From a practical point of view of convenience of this method lies in the fact that all
the ideas are concentrated around the main ideas, and are presented on a single sheet
that allows you to merge all the reactions of this cycle of the chemical properties of
the compounds in a single scheme. It creates convenience for consideration of the
large number of reactions on one sheet of paper, not leafing through the book, that up
to attention.
Graphic organizer «Lotus Flower»: SN reaction of carboxylic acids
HSCoA
РCl3
PCl5
SOCl2
Н3РО4
P2O5
C2H5OH
Example:
Graphic organizer «Lotus Flower»: SN reaction of carboxylic acids
14
7. PRACTICAL TRAINING TASK
Practical task will be executed in minigroups
The technological scheme of the method
Teacher
Students
I stage - Briefing
Briefly presents a practical task, using not Listen to and record.
difficult terms to explain the purpose of
its carrying out.
II stage -Getting acquainted with the instruction of the method
Providing students with instruction on the Get acquainted with the instruction on
implementation of practical tasks.
the implementation of practical tasks
III stage - Implementation of tasks
In the beginning of the operation, make Prepare the necessary equipment and
sure whether they have everything you
reagents, and begin to implement it.
15
need, whether the issues relating to the
process. To watch the progress of the job.
IVstage – presentation of the results
For a few minutes before the expiry time, Mini groups present the results of the
warn of job completion.
work and present
V stage - The final review
According to the obtained data, interpret
the results and draw conclusions
Experience № 1. The opening of the acetic acid
Objective: to study the reactions of nucleophilic substitution of carboxylic acids
Not fulfilled
Completely
(0 points)
correctly
Stages
Actions
1.
2.
3.
Take a clean dry tube
Put in a test tube 10 drops of acetic acid
Add 5-6 drops of water
0
0
0
0,5
0,5
0,5
4.
With the help of litmus paper to determine
the environment
Add 10 drops of solution of sodium
hydroxide
To the mixture add 10 drops of 1%
solution FeCI3
Heated on the stove
Write the equation of reactions and
conclusions in a notebook, explain,
what is the practical application of this
reaction has
Total:
0
1,0
0
0,5
0
0,5
0
0
0,5
3,0
0
7,0
5.
6.
7.
8.
Experience № 2. The formation of insoluble calcium salts of higher fatty acids.
Objective: to study the reactions of nucleophilic substitution of carboxylic acids.
Not fulfilled
Completely
(0 points)
correctly
Stages
Actions
1. Take a clean dry tube
2. Put in a test tube 10 drops of a soap
bubble solution
3. Add 2 drops of the solution CaCl2
4. Mix
5. Write the equation of the reaction and
0
0
1,0
1,0
0
0
0
1,0
1,0
2,0
16
conclusions in a notebook, explain,
what is the practical application of this
reaction has
Total:
0
6,0
Experience № 3. Opening oxalic acid form of calcium salts. Definition of acetic acid
Objective: to study the reactions of nucleophilic substitution of carboxylic acids
Stages
Actions
1. Take a clean dry tube
2. Put a few crystals of oxalic acid in the
tube
3. Add 5-10 drops of water
4. Add to solution 2 drops of CaCl2
5. Write the equation of the reaction and
conclusions in a notebook, explain,
what is the practical application of this
reaction has
Total:
Not fulfilled
(0 points)
Completely
correctly
0
0
1,0
1,0
0
0
1,0
1,0
3,0
0
7,0
8. The analytical part
8.1. Situational tasks:
1. To obtain the functional derivatives of carboxylic
acids
do
not
take
the
carbon
acid
and
its
chlorangadrate. Write the reaction of the receipt of
atsetamide of chlorangadrate carboxylic acid, explain the
mechanism of reaction and confirm the reason why it is
better to use chlorangadrate, and not the acid. (Answer:
the
Reaction
goes
on
SN
mechanism.
Activity
chlorangadrate is explained by the fact that chlorine is
the good of the leaving group. Positive mezomer effect of
chlorine less than the hydroxyl group, acidity more, and
the positive charge at carbon above and SN reaction is
easier.)
2. In the human body many reactions of carboxylic acids are held with the
participation of tioesters. For example, the transformation of choline in acetylcholine,
forming of citric acid from sorrelvinegar acid and atsetilecoenzyme A. Write the
reaction of transformation of choline in acetylcholine, explain the mechanism of
reaction and confirm why nature as a substrate or reagent chose tioesters, and not
esters of carboxylic acids. (Answer: the Reaction goes on SN mechanism. Activity
tioesters is explained by the fact that SR group is a well leaving the group. Positive
mezomer effect SR group less than the hydroxyl group, the radius of the sulphur
17
greater than the radius of oxygen, so the acidity more, and the positive charge at
carbon above and SN reaction is easier.)
3. In the body acilfosfate delivers acil group of alcohol, tiols and substances
containing aminogroupe. Write the reaction of the acetiladenilate and coenzyme A.
Explain the mechanism and why these substances exist in the form of phosphate
anhydride. (Answer: the reaction goes on SN macchanism.So as a phosphate group is
a well-outgoing group, anhydrate group easily hydrolyses and the gap anhydrate link
leads to the formation of a large amount of energy and increases the energy potential
of the process.)
Acetiladenilate
Coenzyme A
Atsetilecoenzyme А
АМF
8.2. The decision of the tests
1. Tests with one correct answer:
1. Depending on the nature of organic radical carboxylic acids can be:
A) one main
B) two main
C) three main
D) a lot of the basic
E) aromatic*
2. During the interaction of carboxyl group of carboxylic acids with urea are formed:
A) ureide acid*
B) urea acid
С) amides
D) amino acids
E) amines
3. Functional derivatives of carboxylic acids type of R-C(O)-NН2 are called:
A) azides
B) amines
C) amides*
18
D) salt
E) amine derived
4. That is the product of the reaction of acetic acid and ethyl alcohol?
A) simple ester
B) half atsetal
In) ethyl acetate*
D) acetic ethyl
E) acetal
5. The reaction of carboxylic acids, going on C-H acid center:
A) eterification
B) atsetilization
C) forming of amides
D) condensation*
E) anomerization
2.Tests with several correct answers:
1. Specify the 4 factors that increase the activity of carboxylic acids and their
derivatives in the reactions of SN:
1. the presence of electron acceptor deputies in the hydrocarbon skeleton of
molecules*
2. the small negative inductive effect of deputies
3. a large amount of positive mesomer effect of deputies
4. the neutrality of the environment
5. the large amount of negative inductive effect of the deputy of the derivatives of
carboxylic acids*
6. decrease of the positive mesomer effect of deputy*
7. availability elektron donor deputies in the hydrocarbon skeleton
8. the presence of acid catalyst*
2. Specify the 5 compounds, participating in the reaction of the saponification:
1. isopropylamine
2. diethyl ester
3. acetilchloride*
4. benzonitrile*
5. aniline
6. ethyl acetate*
7. dimetilketone
8. formaldehyde
9. atsetilecoensim A*
10. propilamide*
3. Specify the 4 factors which depend on the ability of the derivatives of carboxylic
acids to hydrolysis:
1. and the positive charge on the carbonil carbon*
2. the negative charge on the carbonil carbon
3. the nature of the substituents in carboxylic acid*
4. the value of positive inductive effect of the deputy
5. the amount of negative mesomer effect of the deputy
19
6. the amount of negative inductive effect of the deputy*
7. the magnitude of positive mesomer effectof the deputy*
8. strength of the carbon - hydrogen
4. Name the 5 most important functional derivatives of carboxylic acids on - COOH
group
1. salt*
2. amines
3. esters*
4. amides and substituted amides*
5. hydrates
6. complex tioesters*
7. esters
8. disulfides
9. alcohols
10. anhydrides, halides*
5. Specify the 4 of reaction centre in carboxylic acids and their derivatives
1. electrofile center*
2. the potential outgoing group*
3. OH acid center
4. nucleophilic acid center*
5. electrofile the main center
6. NH-acid center
7. CH-acid center*
8. n-the main center
6. Select 4 responses, describing the stages of the reaction mechanism esterification
1. interaction carboxylic acids with proton-catalyst*
2. dissociation of molecules of water*
3. formation of carbanion
4. output catalyst with the formation of ester*
5. electrofile attack on carbanion
6. connection the molecules of water
7. the formation of hydrate
8. alcohol nucleofile attack *
7. Select 4 compounds, which are derivatives of the carbonic acid
1. urea*
2. ureid*
3. glycine
4. stearate
5. phosgene*
6. oliate
7. urethanes*
8. nucleic acids
8. Select 5 acids, which are одноосновными
1. oil*
2. lactate*
20
3. oxalic
4. acetic*
5. amber
6. malon
7. apple
8. formic*
9. benzoic*
10. lemon
9. Specify the 4 the causes of the greater activity tioefireов compared with esters
in the reactions of SN :
1. interaction between carbon atom of carbon and sulphur, and more efficiently than
with oxygen
2. mezomer positive effect of the R-S a group of less than the RO group*
3. alcoxid ion more easy going group than alkilsulfate ion
4. interaction between карбонильным atom of carbon and sulfur less efficiently than
with oxygen*
5. mezomer positive effect of the R-About a group of less than RS group
6. and the positive charge on the карбонильном carbon in tioefireах higher than in
the esters*
7. thiols sour alcohols, i.e. RS - groups are more easily leaving groups*
8. the positive charge on the carbonile carbon in tioesters less, than in the esters
10. Specify the 4 the causes of the greater activity chlorangadrate acetic acid
compared with the acetic acid in the esterification reaction
1. positive charge on carbonil carbon chlorangadrate higher than that of the acid*
2. positive charge on carbonil carbon acids higher than that of the chlorangadrate
3. Cl - ion more poor basis, than OH - ion*
4. mezomer positive effect Cl - ion less than the OH-*
5. OH ion is a weak base, than Cl - ion
6. OH - ion well the outgoing group
7. Cl-ion well the outgoing group*
8. mezomer positive effect of OH - higher than the Cl - ion
11. Bring 4 example of condensation reaction in the body:
1. synthesis of α-amino acids
2. hydrolysis of carbohydrates
3. aldol splitting of α - amino acids*
4. aldol splitting carbohydrates*
5. the reaction between alcohols
6. the reaction tioesters with the formation of a new " links*
7. formation of β- hydroxi acids of α-oxo acids*
8. interaction of carboxylic acids from alcohols
12. Select 3 peculiarities of the structure of ureid of acids :
1. consist of 2 molecules of carbamide
2. contain the balance of urea ( carbamide )*
3. contain the balance of carboxylic acid*
4. are esters of carboxylic acids
21
5. are carbamid derivatives of carboxylic acids
6. are amides of carboxylic acids*
13. Select 3 features structure of ureidacides :
1. contain the balance of urea ( carbamide )*
2. are carboxylic acid amides
3. contain the balance of carboxylic acid*
4. consist of 2 molecules of carbamide
5. are carbamid derivatives of carboxylic acids*
6. are esters of carboxylic acids
3. Multi-level tests
1. Acid interact with alcohols.
A. What is the name of the process of the interaction?
a) condensation
b) atsetilization
c) eterification *
d) hydrogenation
e) dismutation
B. What class of compounds when it is formed?
a) carboxylic acids
b) esters*
c) nucleic acids
d) amides
e) cianhydrates
C. What the mechanism of the reaction is typical for this process?
a) nucleophilic substitution*
b) electrophilic substitution
c) electrophilic accession
d) nucleophilic accession
e) the radical replacement
2. In the exchange of substances in the body are involved representatives of the
esters, amides, complex tioefireов, anhydrides and all of them during the
hydrolysis to form one and the same class of organic compounds.
A. The name of this class of compounds:
a) saturated hydrocarbons
b) ethylenic hydrocarbons
c) heterofunctional connection
d) acetylene hydrocarbons
e) carboxylic acids*
B. What is the mechanism of reactions is more characteristic for this group of
compounds?
a) nucleophilic substitution*
b) electrophilic substitution
c) electrophilic accession
d) nucleophilic accession
e) the radical replacement
22
C. Specify a factor contributes to the acceleration of the reactions coming to this
mechanism?
a) the presence of donor substituent in a molecule
b) an acidic catalyst*
c) cooling the reaction mixture
d) the dilution of the solution
e) reduction of the pressure in the system
3. In the body of coenzyme A activates carboxylic acids, turning them into
reactionary capable esters of tiols.
A. Why thioethers, and not the usual esters of selected nature as vectors of the acil
groups?
a) tioesters have more than the basic properties than conventional esters
b) tioesters more active in the reactions of electrophilic substitution
c) tioesters more active in the reactions of nucleophilic substitution*
d) alkil sulfide-ions are bad leaving groups than alcoxid-ions
e) alcoxid-ions esters are more easy to go groups than alkil sulfide-ions
B. What is associated with their effectiveness in the reactions of metabolism?
a) and the partial positive charge on the carbon atom in the esters higher than in
tioesters
b) and the partial positive charge on the carbon atom in tioesters above, than in the
esters*
c) and a partial negative charge on the carbon atom in tioesters higher than in the
esters
d) alcoxid ions easily replaced than alkil sulfide -ions
e) esters easily hydrolysable by, than complex tioesters
C. What caused this factor?
a) RS-group gives more +M-effect than RO-group
b) +M-effect RS-group and RO-groups are equal to each other
c) RS-group gives no +M-effect
d) RS-group provides a lower +M-effect than RO-group*
e) RO-group gives no +M-effect
4. While studying the structure and properties of nucleic acids, fats and other
biologically active compounds often found сложноэфирная connection.
A. When interacting any connections it is formed?
a) acids and amines
b) acids and alcohols*
c) aldehydes and alcohols
d) ketones and amines
e) ketones and alcohols
B. Among the functional groups it is formed?
a) aldehyde and hydroxyl
b) ketone and hydroxyl
c) carboxyl and amino group
d) nitro group and carboxyl
e) carboxyl and hydroxyl*
23
Estimation
№
Achievement
C. The environment in which it hydrolyses?
a) neutral
b) in the environment of alkali metals
c) acid and alkaline*
d) in the environment of polar solvent
e) in the environment of a non-polar solvent
5. The connection is the most important nitrogen the end product of metabolism
and is a derivative of carbonic acid.
A. What is the connection?
a) ureid acides
b) ureid of acid
c) biuret
d) guanidine
e) urea*
B. How derivative of carbonic acid it is?
a) chlorangadrate
b) diamide*
c) amide
d) ester
e) anhydride
In. What products it gives the hydrolysis?
a) acid and ureid
b) acid and alcohol
c) carbon dioxide and ammonia*
d) two acid
e) acid and amin
9. Criteria for the evaluation of the current control
The level of student knowledge
Theoretical part: the Student gives the full, complete with from different literature sources
reply on the topic of classes, the volume of knowledge goes beyond the limits of the
program. Learned all the literary data, proposed in the programme and familiar with the
additional literature. The job carries out in time and qualitatively. Actively participates in
the discussion of themes and different views on the vision of the subject, confidently
asserting its views on one or another debated issue. Do not make mistakes in writing
formulas, equations and mechanisms of reactions, independently makes conclusions and
make decisions. Actively and creatively participate in interactive teaching methods, the
questions gives a comprehensive and well-grounded responses.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. Summary compiled logically correct
and includes a fully open questions text is presented systematically identifies the main
literature and additional sources of information.
Preparation of the abstract. In the collection of the material the student used, in addition to
24
Excellent «5»
96-100
1.
Excellent «5»
91-95
2.
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), deeply analyzed and systematized. The theme of the essay is
disclosed fully and completely, the text is presented in a logical sequence, conclusions are
made correctly and feel the creative approach.
Creative work. The student correctly filled with graphic organizers, tables, to their
compilation approached creatively and reasonably.
Training of scientific articles, theses and reports at:
Students spend an independent experimental work in SSA, designed in work-book,
independently spent their discussion and processed statistical data, made a reasonable,
logical faithful, educated conclusions. Of educational and scientific literature, the results
of scientific-research works, articles, theses and monographs, as well as other sources of
information a student gathered theoretical material on a theme of work, analyzed and
systematized all the literary data. Prepared by the article, thesis or report are based on the
scientific results of the self-experimental work and the analysis of literary data collected
by the student.
Practical part:Mastered all the practical skills, apply the received theoretical knowledge
in carrying out of experimental works. Without errors carries out step-by-step
implementation of reactions, correctly writes equations of the reactions, substantiate and
make the right conclusions.
The analytical part: Creativity and the right thinks when solving situational tasks and tests
give accurate and logical answers.
Theoretical part: a Student gives a complete answer on the topic of classes, the volume of
knowledge of the limits of the program. Learned all the literary data, proposed in the
programme and familiar with the additional literature. The job carries out in time and
qualitatively. Actively participates in the discussion of themes and different views on the
vision of the subject, confidently asserting its views on one or another debated issue. Do
not make mistakes in writing formulas, equations and mechanisms of reactions,
independently makes conclusions and make decisions. Actively and creatively participate
in interactive teaching methods, the questions gives a comprehensive and well-grounded
responses.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. Summary compiled logically correct
and includes a fully open questions text is presented systematically identifies the main
literature and additional sources of information.
Preparation of the abstract. In the collection of the material the student used, in addition to
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), deeply analyzed and systematized. The theme of the essay is
disclosed fully and completely, the text is presented in a logical sequence, conclusions are
made correctly and feel the creative approach.
Creative work. The student correctly filled with graphic organizers, tables, to their
compilation approached creatively and reasonably.
Training of scientific articles, theses and reports at:
Students spend an independent experimental work in SSA, designed in work-book,
independently spent their discussion and processed statistical data, made a reasonable,
logical faithful, educated conclusions. Of educational and scientific literature, the results of
scientific-research works, articles, theses and monographs, as well as other sources of
information a student gathered theoretical material on a theme of work, analyzed and
systematized all the literary data. Prepared by the article, thesis or report are based on the
scientific results of the self-experimental work and the analysis of literary data collected by
the student.
Practical part:Mastered all the practical skills, apply the received theoretical knowledge in
25
Excellent «5»
Theoretical part: a Student gives a complete answer on the topic of classes, the volume of
knowledge in the programme. Learned all the literary data, proposed in the programme and
familiar with the additional literature. The job carries out in time and qualitatively. Actively
participates in the discussion of themes and different views on the vision of the subject,
confidently asserting its views on one or another debated issue. Do not make mistakes in
writing formulas, equations and mechanisms of reactions, independently makes conclusions
and make decisions. Actively and creatively participate in interactive teaching methods, the
questions gives a comprehensive and well-grounded responses.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. Summary compiled logically correct
and includes a fully open questions text is presented systematically identifies the main
literature and additional sources of information.
Preparation of the abstract. In the collection of the material the student used, in addition to
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), properly analyzed and systematized. The theme of the essay
is disclosed fully and completely, the text is presented in a logical sequence, conclusions
are made correctly and feel the creative approach.
Creative work. The student correctly filled with graphic organizers, tables, to their
compilation approached creatively and reasonably.
Practical part:Mastered all the practical skills, apply the received theoretical knowledge in
carrying out of experimental works. Without errors carries out step-by-step implementation
of reactions, correctly writes equations of the reactions, substantiate and make the right
conclusions.
The analytical part: Correctly solves situational tasks and tests give accurate and logical
answers.
Good «4»
carrying out of experimental works. Without errors carries out step-by-step implementation
of reactions, correctly writes equations of the reactions, substantiate and make the right
conclusions.
The analytical part: Creativity and the right thinks when solving situational tasks and tests
give accurate and logical answers.
Theoretical part: a Student gives a complete answer on the topic of classes, the volume of
knowledge in the programme, is responsible confidently. Learned all the literary data,
proposed in the programme and familiar with the additional literature. Job performs on time
and correctly. Actively participates in the discussion of themes and different views on the
vision of the subject, confidently asserting its views on one or another debated issue. In
writing formulas, equations and reaction mechanisms, allows for minor errors. Actively
participating in the interactive methods of training, to questions gives the most part correct
answers.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. The summary includes all open
questions, the text is presented systematically identifies the main literature and additional
sources of information.
Preparation of the abstract. In the collection of the material the student used, in addition to
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), analyzed and systematized. The theme of the essay is opened,
the conclusions are made correctly.
Creative work. The student correctly filled with graphic organizers, the tables are filled in
correctly and completely.
Practical part:Mastered all the practical skills, apply the received theoretical knowledge in
carrying out of experimental works. Without errors carries out step-by-step implementation
of reactions by writing the equations allows 1-2 small mistakes, substantiate and make the
right conclusions.
86-90
3.
81-85
4.
26
The analytical part: Correctly solves situational tasks and tests give accurate and logical
answers.
Good 4»
76-80
5.
The analytical part: Correctly solves situational tasks and tests give accurate and
logical answers.
Theoretical part: the Amount of the student's knowledge in the programme, is
responsible confidently. Learned all of the main literary sources. Job performs on
time. Actively participates in the discussion of themes and different views on the
vision of the subject. In writing formulas, equations and reaction mechanisms,
allows for 2-3 errors. Participating in the interactive methods of training, to
questions gives greater part of the correct answers, but some of the answers may
not justify.
Good «4»
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. The summary includes all open
questions, the text is presented systematically identifies the main literature and sources of
information.
Preparation of the abstract. In the collection of the material the student used, in addition to
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), analyzed and systematized. The theme of the essay is opened,
the conclusions are made correctly.
Creative work. The student correctly filled with graphic organizers, the tables are filled in
correctly and completely.
Practical part: Mastered all the practical skills, apply the received theoretical
knowledge in carrying out of experimental works. Without errors carries out stepby-step implementation of reactions by writing the equations allows for 2-3 small
mistakes, substantiate and make the right conclusions.
The analytical part: Correctly solves situational tasks and tests, but is difficult to
substantiate the answer.
Theoretical part: the Amount of the student's knowledge is 60-70% of the
programme. Learned the main literary sources. Has an idea about the structure
and properties of the considered compounds, further questions the answers are
incomplete. Participating in the interactive methods of training, to questions gives
66-70
Satisfact
orily
«3»
71-75
6.
7.
Theoretical part: the Amount of the student's knowledge in the programme, is responsible
confidently. Learned all of the main literary sources. Job performs on time. Actively
participates in the discussion of themes and different views on the vision of the subject. In
writing formulas, equations and reaction mechanisms, allows 1-2 errors. Actively
participating in the interactive methods of training, to questions gives greater part of the
correct answers, but also allows for minor errors.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. The summary includes all open
questions, the text is presented systematically identifies the main literature and sources of
information.
Preparation of the abstract. In the collection of the material the student used, in addition to
the primary literature, additional sources of information (монографири, scientific and
methodological articles and reports, information from Internet sources, materials of
electronic бибилиотек, etc.), analyzed and systematized. The theme of the essay is opened,
the conclusions are made correctly.
Creative work. The student correctly filled with graphic organizers, the tables are filled in
correctly and completely.
Practical part:Mastered all the practical skills, apply the received theoretical knowledge in
carrying out of experimental works. Without errors carries out step-by-step implementation
of reactions by writing the equations allows 1-2 small mistakes, substantiate and make the
right conclusions.
27
greater part of the right answers, but the answers allows a number of errors
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. The summary includes all open
questions, but there is no systematic in the presentation of text, specified the main literature
and sources of information.
Preparation of the abstract. The student uses only the main sources of literature, analyzed
and made some conclusions. The topic of the abstract disclosed, but there are some
drawbacks.
Creative work. Student filled with graphic organizers, but difficult in the justification of the
responses, when filling in tables admitted some disadvantages.
Practical part: Mastered practical skills, but allows some errors. Carries out step-by-step
implementation of reactions by writing the equations allows 3-4 mistakes, but difficult to
substantiate and conclusions.
The analytical part: When solving situational tasks and tests allow some errors.
Theoretical part: the Amount of the student's knowledge is 55-60% of the
programme. Learned the main literary sources. Has an idea about the structure
and properties of the considered compounds, further questions the answers are
incomplete. Inactive in interactive methods of training, to some of the questions
the answers, but the answers makes mistakes.
Satisfactorily «3»
61-65
8.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. The summary includes all open
questions, but there is no systematic in the presentation of text, specified the main literature
and sources of information.
Preparation of the abstract. The student uses only the main sources of literature, analyzed
and made some conclusions. The topic of the abstract disclosed, but there are a number of
shortcomings.
Creative work. Student filled with graphic organizers, but mistakes have been made, does
not justify the answers, when filling in tables admitted shortcomings.
Practical part: Mastered practical skills, but allows some errors. Is wrong with the
carrying out step-by-step implementation of reactions by writing the equations
allows 3-4 gross errors, but difficult to substantiate and conclusions.
The analytical part: When solving situational tasks and tests allow some errors.
Theoretical part: the Volume of knowledge of a student is 50-55 per cent of the
programme. For additional questions, not answers. Partially used literature. Has
an idea about the structure and properties of the considered compounds, in
response to the questions allows a lot of mistakes. Inactive in interactive teaching
methods, the questions gives a superficial answers.
Satisfactorily «3»
55-60
9.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
Self-absorption of the topic and writing a synopsis. In summary all the questions do not
disclosed, there is no systematic in the presentation of the text, not specified the main
literature and sources of information.
Preparation of the abstract. The student uses only the main sources of literature, but there is
no systematic and analysis. The theme of the essay is not disclosed.
Creative work. Student filled with graphic organizers, but may not work alone, can not
justify the answers, when filling in tables admitted shortcomings.
Practical part: Mastered practical skills in part, cannot independently carry out
laboratory work. Is wrong with the carrying out step-by-step implementation of
reactions by writing the equations admits many gross errors, does Not make
independent conclusions.
The analytical part: When solving situational tasks and tests, there is no
independence.
28
Неудовлет unsatisfactory ьно «2»
unsatisfactory «2»
50-54
10.
36-40
13
unsatisfactory
unsatisfactory «2»
41-45
12
Theoretical part: the Volume of knowledge of a student is 30-40% of the
programme. Is not clear on the theoretical aspects of the topic. For additional
questions, not answers. Not mastered the basic literature. Has a slight idea about
the structure and properties of the considered compounds, but practically does not
respond to questions. Does not perform in time job data in the lesson. Does not
participate in interactive teaching methods.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
For the abstract and the abstract assembled a small stuff, but a lot of mistakes when writing.
Graphic organizers are not compiled.
Practical part: Mastered practical skills in part, cannot independently carry out laboratory
work. Cannot independently carry out step-by-step implementation of reactions by writing
the equations admits many gross errors, does Not make independent conclusions.
The analytical part: can't decide situational tasks and tests.
Theoretical part: the Volume of knowledge of a student is 20-30% of the programme. Is
not clear on the theoretical aspects of the topic. For additional questions, not answers. Not
mastered the basic literature. Has a slight idea about the structure and properties of the
considered compounds, but practically does not respond to questions. Does not perform in
time jobs, data on the lesson. Does not participate in interactive teaching methods, the
questions can't answer. By the end of session acquires some ideas for names, formulas and
conclusions of the studies.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
For the abstract and the abstract assembled a small stuff, but a lot of mistakes when writing.
Graphic organizers are not compiled.
Practical part: Mastered practical skills in part, cannot independently carry out laboratory
work. Cannot independently carry out step-by-step implementation of reactions by writing
the equations admits many gross errors, does Not make independent conclusions.
The analytical part: can't decide situational tasks and tests.
Theoretical part: the Volume of knowledge of a student is 20% of the programme. Is not
clear on the theoretical aspects of the topic. For additional questions, not answers. Not
mastered the basic literature. Has no idea about the structure and properties of the
considered compounds, does not answer the questions. Does not perform in time jobs, data
on the lesson. Does not participate in interactive teaching methods, the questions can't
answer. By the end of session acquires some ideas for names, formulas and conclusions of
the studies.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
For the abstract and the abstract assembled a little material, but not written. Graphic
organizers are not compiled.
Practical part: Mastered practical skills in part, cannot independently carry out laboratory
work. Cannot independently carry out step-by-step implementation of reactions do not
know how to write equations,does not make independent conclusions.
The analytical part: can't decide situational tasks and tests.
Theoretical part: the Volume of knowledge of a student is 10% of the programme. Is not
clear on the theoretical aspects of the topic. For additional questions, not answers. Not
mastered the basic literature. Has no idea about the structure and properties of the
considered compounds, does not answer the questions. Does not perform in time jobs, data
on the lesson. Does not participate in interactive teaching methods, the questions can't
answer. By the end of session acquires some ideas for names, formulas and conclusions of
the studies.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
For the abstract and the abstract assembled a little material, but not written. Graphic
organizers are not compiled.
29
Practical part: Mastered practical skills in part, cannot independently carry out laboratory
work. Cannot independently carry out step-by-step implementation of reactions do not
know how to write equations,does not make independent conclusions.
The analytical part: can't decide situational tasks and tests.
unsatisfactory «2»
31-35
14.
The theoretical
part of the
The SIW
The practical
part of the
The analytical
part of
Theoretical part: could not answer definitely. Has no idea on the theoretical aspects of the
topic. Not mastered the basic literature. Has no idea about the structure and properties of
the considered compounds, does not answer the questions. Does not perform in time jobs,
data on the lesson. Does not participate in interactive teaching methods, the questions can't
answer. By the end of session acquires some ideas for names, formulas and conclusions of
the studies.
The form of independent work: self-learning topics, preparation of the abstract, scientific
articles, theses and reports.
For the abstract and the abstract assembled a little material, but not written. Graphic
organizers are not compiled.
Practical part: Mastered practical skills in part, cannot independently carry out laboratory
work. Cannot independently carry out step-by-step implementation of reactions do not
know how to write equations and not draw conclusions.
The analytical part: can't decide situational tasks and tests.
96-100
44-45
91-95
42-43
86-90
38-39
81-85
36-37
76-80
33-34
71-75
31-32
66-70
29-30
61-65
27-28
55-60
26-27
31-54
12-25
0-30
0-11
9-10
19-20
8-9
18-19
8-9
18-19
7-8
17-18
7-8
16-17
6-7
15-16
6-7
14-15
6-7
13-14
6-7
10-11
4-5
6-9
0-4
0-6
24-25
23-24
22-23
21-22
20-21
19-20
17-18
15-16
13-15
9-15
9
10. Literature
Summary:
1. N.A.Tyukavkina. Bioorganic Chemistry, Moscow, 2004
2. N.A.Tyukavkina. A guide to laboratory work on
Bioorganic Chemistry, Moscow, 1999
General:
1. Sh.U.Abdullaev, A.D.Dzhuraev, U.A.Boltabaev and other management to practical
training in Bioorganic Chemistry, Tashkent, 1982
1. Shris Conoley, Phil Hills. Chemistry. London, 1998.
2. B.N.Stepanenko. Organic Chemistry. 1980
3. Z.Gauptman. Organic chemistry, M. 1983
5. P. Sykes - Mechanisms of Reactions in Organic Chemistry, 1977
6. Yu.A.Rayls. Fundamentals of Organic Chemistry, M.1993.
7. Sources of information from the Internet:
30
www.tma.uzsi.net.; www mail.ru; http:// www. doctor. Ru / medinfo; http://medinfo.
home. ml. org. ; Http://www.bankreferatov.ru; http://www. 5 ballov.ru; http://www.
referat. Ru
C: \ Documents and Settings \ Administrator \ My Documents \ Organik_KIMYO
C: \ Documents and Settings \ Administrator \ My Documents \ Tutorial organic
himii_files
www.tma.uzsi.net.
Application to the method of «Brainstorming»:
Appendix №1
Questions blitz-poll:
Theacher
1. Classification and nomenclature of carboxylic acids, carboxylic
acids of an organism
2. Types of reactions of carboxylic acids
3. How to increase the reactivity of carboxylic acids?
4. What substaces come into reaction of carboxylic acids?
5. The product of the reaction with alcohols
6. The product of the reaction with tiols
7. The product of the reaction with ammonia
8. The product of the reaction with phosphorus anhydride
9. The product of the reaction with sodium hydroxide
10. The product reacts with phosphoric acid
11. The product of the reaction with phosphorus chloride
12. The product of the reaction with coenzyme A
1З. The environment in which hydrolysable by esters?
14. The environment in which hydrolysable by anhydrides?
15. The environment in which hydrolysable by amide connection?
16. The environment in which hydrolysable by halogenanhydrates
connection?
17. As a proven mechanism of the reaction of the esterification?
18. The product of hydrolysis of fats
19. What are the consequences of electron donor deputies on the
reactivity of carbon acids?
20. What are the consequences of электроноакцепторные
deputies on the reactivity of carbon acids?
Student
Answer
questions
quickly and
briefly
Appendix № 2
Small group
The number of
group
members and
experts
Problems to be solved in small
groups
31
1-group
4 (1 the expert)
2-group
4 (1 the expert)
3-group
4 (1 the expert)
4- group
4 (1 the expert)
1.
The reactionary centers in
molecules
carboxil
containing
connections. The reactivity and the
factors influencing it. The General
scheme of the mechanism of
nucleophilic substitution
1. The reaction of formation of esters
and tioefireов carboxylic acids and
their mechanism
1. Reactions of education and halogen
anhydrides of carboxylic acids and
their mechanism
1. Reactions of education amides,
hydrazides of carboxylic acids and
it’s mecchanisim
Appendix № 3
Independent work of the student, designed as an abstract and (or) the presentation.
32