Chemistry 250. Fundamentals of Organic Chemistry.
(MCK 213, 8:00-8:50 MWF)
Text: Katherine J. Denniston, Joseph J. Topping, and Robert L. Caret, “General, Organic, and
Biochemistry”, seventh edition, 2011, chapters ten through fifteen. This textbook is also be
used for Chemistry 315 and for Chemistry 125.
Professor: Joseph M. Crockett
Office: McKinney 307
Phone: 828-5431 (office), 828-6480 (home, not after 10 pm)
Email: jcrocket@bridgewater.edu
Web: www.bridgewater.edu/~jcrocket
Course description: An overview of the functional groups present in and the reactivity of organic molecules using
biological examples, and the three-dimensional structures of the molecules.
College Honor Code: Ethics, honor, and integrity are the fundamental principles at the core of the Bridgewater College
experience. Our community can only flourish in an environment of trust and respect and these notions of personal honor,
integrity, and faith are the fundamentals of the Bridgewater Honor System. The Code of Honor prohibits lying, cheating,
and stealing and Bridgewater College’s commitment to ethics, integrity, and values is embodied in the Code of Ethics.
Violation of these Codes demonstrates harm to the community and an all-student Honor Council administers regulation of
this Honor System. It is the goal of our Honor Council to assist in the development of students’ ethical and moral base.
(page 43 of current college catalog).
Notification of Student Support Services: The Academic Support Center, located in Bicknell House, promotes learning
skills and personal development through academic counseling, advising, tutoring services, disability services, and a
transition program for selected new students. Further information may be found at
http://www.bridgewater.edu/student-life/services/academic-support-center
Grading: Your grade will be based on four tests (50%), problem sets (10%), a cumulative final exam (15%), and the lab
(25%). The letter grades will be assigned on a 10 point scale, above 89.5 is an A, above 79.5 is a B, above 69.5 is a C, and
above 59.5 is a D. I do use the +/- scale. For example, a B+ is 88.0 to 89.5 and an A- is 89.5 to 91.0. I do reserve the right to
lower the scales if I choose, i.e. an 87 could become a B+ but a 92 will always be an A. Any decision on lowering the scales
will be made at the end of the term after all work is graded. In keeping with department policy, you must earn a passing
grade on BOTH the lecture component and on the lab component of the course in order to get a passing grade for the
compete class.
Problem sets. The problem sets will be a series of problems that will be handed out in class and are due on the date
indicated on the syllabus. They may be turned in early so there is no excuse for not submitting the work. I will drop the two
lowest submitted sets. Each problem set will be twenty points.
Attendance: I expect every student to be at every class. If you must miss a class for a scheduled absence, I will be notified
by you in advance. For an emergency, you should call and leave me a message on my office phone if time permits. We can
discuss missed work when the emergency passes. Tests can start at 7:30 if you wish additional time. Tests should take
about 40-45 minutes. When the test is completed, I will distribute the key to test. The key may contain more information
than asked for on the test. I do not give makeup tests. Test absences will be handled on an individual basis. I do not give
make-up tests and if you must be absent, I will notified by you in advance. Multiple absences from tests or multiple
absences when your grade is failing are considered excessive.
I consider all external communication devices (ie cell phones) to be an irritant during class. You will silence these devices
before class. Any communication during class may result in a lower grade. On tests you will NOT be allowed to use
calculators or any other electronic devices (i. e., ipods). If these are out during the test, I will not grade your test and
you will get a zero.
Classwork: As you go through the text I expect you to read each day’s assignment prior to class and to work the problems
associated with those sections. I will expect you to work all of the assigned problems at the end of each chapter. The more
problems you attempt, the better you will do in the class. To properly work the problems and to get the most benefit out of
the problems and the class, first write out your solution and check your answers. Work alone, but talk over the problems
you cannot do with another student in the class. Work in a study group is encouraged, but remember that on the tests you
will be working alone. When you cannot work a problem or you cannot get “the book answer”, come and ask me. My
office hours are ~7:30 to 4:00 except for specifically marked times. There will be a sheet on my door each week of times
when I am available. You can sign up for an appointment at any of these times.
For lab you will need a bound, stitched notebook and safety goggles. The goggles and lab manuals can be purchased from
the secretary (MCK 161) this week (prices are posted at her office and at my office). Goggles purchased from other sources
must meet the ANSI standards and be approved by me. Contacts are not as safe and should not be worn in lab without
notifying the professor. The lab is considered an important integral part of the course. If you fail the lab for any reason, you
will fail the course. Your first lab will be on Monday, September 3, or Tuesday, September 4. This is a check in lab to get
you introduced to the lab room. You will need the manual for this lab.
Safety: A safety test will be given during the first week of school and those times are posted. If you do not pass the test,
you will be required to attend the safety seminar and those times will also be posted. If you have not taken the safety
seminar you do not take the test, but are required to take the seminar. The safety grade is the first lab grade. Failure to
complete the safety requirement will result in a zero for your first lab grade.
Periodic Table: There is no periodic table in the classroom. I will expect you to know the positions, symbols, and names of
the following. You will not need to know atomic weights.
H
Li
Na
B
Al
Mg
Mn
Cr
C
Si
N
P
O
S
Se
F
Cl
Br
I
Chem 250 – Daily Schedule MWF
Day
Date
Material
Graded work
W
Aug 26
Section 10.1
Bonding – ionic and covalent (multiple bonds) –sigma bonds
Octet rule – applied to C, N, O
Functional groups – know all in Table 10.2
Be able to draw molecules in bondline, condensed, and structural formula
Be able to do problems at the end of the chapter: 9-44
F
Aug 28
10.2. Nomenclature
Know the stem names through 10 carbons (Table 10.7)
Know prefixes (Tables 10.5 and 10.6)
Know chloro, bromo, iodo, and fluoro
Be able to do problems at the end of the chapter: 45-70.
Problem Set
M
Aug 31
16.3 Stereoisomers – enantiomers, diastereomers, and meso compounds.
Be able to draw Fisher projections.
What are the differences and similarities between different stereoisomers?
Racemic mixtures.
Be able to do problems at the end of the chapter: 33-52.
Problem Set
W
Sept 2
Continue and catch up
F
Sept 4
10.3. Cycloalkanes – nomenclature and stereoisomers.
Cis / trans isomerism.
Be able to do problems at the end of the chapter: 71-88.
Problem Set
M
Sept 7
10.4. Conformational (rotational) isomers.
Newman projections – Eclipsed and staggered, staggered and gauche
conformations.
Conformations of rings – butterfly, envelope, boat, and chair
Axial and equatorial positions on a chair (six membered ring only).
Be able to do problems at the end of the chapter: 89-96.
Problem Set
W
Sept 9
10.5. Reactions of alkanes.
Bromination and chlorination – 3o positions are most reactive.
Combustion with excess oxygen to carbon dioxide and water.
Be able to do problems at the end of the chapter: 97-108.
F
Sept 11
Substitution reactions of halides
There are two types of substitution, SN1 and SN2, depending on the
mechanism and the order of the reactants.
Be able to do problems on handout.
M
Sept 14
Continue and catchup
W
Sept 16
Problem Set
Test One
F
Sept 18
11.1 – Structure and properties of alkenes and alkynes – sigma and pi bonds.
What is an unsaturated hydrocarbon?
Be able to do problems at the end of the chapter: 23-36
M
Sept 21
11.2 - Nomenclature
Dienes can be conjugated, cumulated, or isolated
You do not need to name molecules with both a triple bond and a double
bond as suffixes. Know the vinyl group.
Be able to do problems at the end of the chapter: 37-48
W
Sept 23
11.3. Cis, trans isomerization of alkenes.
Be able to do problems at the end of the chapter: 49-54
F
Sept 25
Resonance – movement of nonbonding and pi electrons.
There are three basic types of resonance in molecules. Understanding the
forms will significantly aid you in understanding a molecules reactivity.
Problems handout.
Problem Set
M
Sept 28
Preparation of alkenes – E1 and E2 reactions.
Preparation of an alkene by elimination from an alkyl halide (E2) or
dehydration of an alcohol (E1).
Problems handout.
Problem Set
W
Sept 30
11.5. Reactions of alkenes and alkynes.
Addition of HX, H2O, X2, and H2.
Markovnikov addition.
Be able to do problems at the end of the chapter: 55-84.
F
Oct 2
11.6. Aromatics and reactions.
Know benzene, naphthalene, anthracene, phenanthrene, and biphenyl
Reactions include sulfonations, halogenation, and nitration
Be able to do problems at the end of the chapter: 85-98.
M
Oct 5
Fall break – no class
W
Oct 7
11.7. Heterocyclic aromatics.
A handout of important species which are related to biochemistry.
Be able to do problems at the end of the chapter: 99-102.
F
Oct 9
Continue and catch-up.
M
Oct 12
W
Oct 14
12.1. Alcohols – structures and properties.
Hydrogen bonding – how does it affect solubility and boiling point.
12.4. Classification of alcohols - primary, secondary, tertiary, and benzylic.
Be able to do problems at the end of the chapter: 13-18, 37-44.
F
Oct 16
12.2. Alcohol nomenclature
Be able to do problems at the end of the chapter: 19-36.
Midterm grades due today
Problem Set
Problem Set
Problem Set
Test Two
Problem Set
M
Oct 19
12.5. Reactions of alcohols.
Preparation from alkenes or halides (already covered) or by reduction of
aldehydes or ketones.
Reaction of alcohol by dehydration (already covered) and with HCl or HBr.
Be able to do problems at the end of the chapter: 45-66.
Problem Set
W
Oct 21
12.6. Oxidation and reduction reactions.
Oxidation is an increase in the number of bonds to oxygen or a decrease in
the number of bonds to hydrogen.
Oxidation – reagent is a metal oxide, oxygen, a peroxide, or ozone.
Reduction is an increase in the number of bonds to hydrogen or a decrease in
the number of bonds to oxygen.
Oxidation – reagent is a metal oxide, oxygen, a peroxide, or ozone.
Reduction – reagent is H2, H- (followed by H+), or 2 H+ and 2 e-.
Be able to do problems at the end of the chapter: 67-70.
F
Oct 23
12.7. Phenols. An OH on an aromatic ring.
Weak acids – what affects the acidity (an acid is a proton donor).
Be able to do problems at the end of the chapter: 71-76.
M
Oct 26
12.8. Ethers – simple nomenclature and preparation from an alcohol.
12.9. Thiols – smell – more acidic than alcohols.
Be able to do problems at the end of the chapter: 77-94.
W
Oct 28
13.1. Properties of aldehydes and ketones. Why don’t ketones hydogen bond
with aldehydes?
13.2. Nomenclature – aldehydes have priority over ketones because they are
more reactive.
Be able to do problems at the end of the chapter: 17-44.
F
Oct 30
Continue and catch up
M
Nov 2
W
Nov 4
13.4 Reactions of aldehydes and ketones.
Oxidation and reduction.
Addition of water, alcohols, and amines.
Aldol reactions.
Be able to do problems at the end of the chapter: 45-92.
F
Nov 6
Continue
Problem Set
M
Nov 9
14.1. Acids – nomenclature (common names are important!).
Know the common names for acids as on the handout.
What affects the acidity of an acid – why is a carboxylic acid stronger than a
phenol or alcohol?
Be able to do problems at the end of the chapter: 15-60
Problem Set
W
Nov 11
Continue and catch up – reactions of acids.
Preparation from a primary alcohol, aldehyde, carboxylation of a Grignard, or
hydrolysis of a nitrile.
Reaction with an alcohol (to form an ester), base (to form a carboxylate, or an
amine (to form an amide).
Reduction to form a primary alcohol.
Problem set.
Problem Set
Problem Set
Test Three
F
Nov 13
14.2. Esters.
Nomenclature, preparation from an acid or acid chloride, reduction to form an
alcohol.
Be able to do problems at the end of the chapter: 61-86
M
Nov 16
14.3. Acid chlorides and anhydrides.
Reactions with water, alcohols, amines, or hydroxide.
Be able to do problems at the end of the chapter: 87-110
W
Nov 18
15.1. Amines and basicity.
How are amines classified as primary, secondary, or tertiary?
A base is a proton acceptor. What affects the basicity of an amine?
What is an ammonium salt?
Be able to do problems at the end of the chapter: 11-42.
F
M
Nov 20
Nov 23
Continue
W
Nov 25
Thanksgiving break – no class.
F
Nov 27
Thanksgiving break – no class.
M
Nov 30
15.2. Heterocyclics. What is an alkaloid?
Be able to do problems at the end of the chapter: 43-46.
W
Dec 2
15.3. Amides. How does an amide differ in reactivity from an amine?
Be able to do problems at the end of the chapter: 47-70.
F
Dec 4
Last Day of class
Problem Set
Problem Set
Test Four
Help Session – tba
Final Exam – tba
Problem Set
Laboratory schedule. There are three lab sections. The first section meets from 12:00 to 2:00 on Monday. The
second section meets from 2:15 to 4:15 on Monday. The third section meets from 11:00 to 1:00 on Tuesday
morning. The pre-labs will be held in MCK 305.
#
Day
Date
Material
Safety Test – see posted times in McKinney
L0
L1
M
T
08-31
09-01
Lab Check in. Procedures and Policies.
L2
M
T
09-07
09-08
Experiment One. Models and Functional groups.
L3
M
T
09-14
09-15
Experiment Two. Qualitative Analysis. Distillation.
L4
M
T
09-21
09-22
Infrared Spectroscopy – in room 333.
L5
M
T
09-28
09-29
Experiment Two. Functional Group tests.
L6
M
T
10-05
10-06
Fall Break
M
T
10-12
10-13
Experiment Four. Isomerization of Maleic acid to Fumaric acid.
L6
M
T
10-19
10-20
Experiment Three. Dehydration of 2-methylcyclohexanol.
L7
M
T
10-26
10-27
Experiment Eight. Chromatography.
L8
M
T
11-02
11-03
Experiment Five. Hydrolysis of Methyl benzoate.
L9
M
T
11-09
11-10
Experiment Six. Determination of Vitamin C.
L10
M
T
11-16
11-17
Experiment Seven. Preparation Aspirin.
L11
M
T
11-23
11-24
Lab check-out and cleanup.
L12
M
T
11-30
12-01
No lab
For each experiment, the notebooks will be collected in class on Wednesday and returned in class on Friday. The
polarimetry and chromatography labs will be ready later.