Name
REPORT
1
1)
Crystallization and
Determination of Melting
and Boiling Points
Instructor
Date
Group
†
†
BSAC
ISE
Solid sample number………………………………………..
Before crystallization,
2)
Weight of unpurified sample
=…………..…………..…g
Melting point (report as a range)
=…………...……………...oC
Suitable solvent for crystallization
= ……………………………………………..
After crystallization,
Weight of purified sample
=…………….…………..g
%recovery
=……..…………………………………………...…
……………………………..................................
3)
Melting point (report as a range)
=…………...……………...oC
Liquid unknown sample number
=………………………….
Temperature when you see straight line bubbles
=……………………....oC
Temperature when you see liquid goes into capillary
=……...………….…… oC
Boiling point
4)
=........................................oC
Conclusion and Discussion
Page 1 of 2
Question
1)
Which temperature would be the boiling point of the unknown sample; temperature
when you see the straight line bubbles or temperature when you see the liquid goes
into capillary tube? Rational your answer.
2)
What could be the causes for error in this experiment?
3)
Does the size of crystals correlate to the purity of product? How?
Page 2 of 2
Name
REPORT
2
1)
Extraction and Simple
Distillation
Instructor
Date
Group
†
†
BSAC
ISE
After adding the 10% NaOH to the CH2Cl2 solution:
In the upper phase, there was…………………….... dissolved in…………….…………
In the lower phase, there was…………………….... dissolved in …………….…………
2)
Temperature at which you observed the CH2Cl2 coming into the conical flask
=………….............................oC
3)
Weight of isolated benzoin
%recovery
4)
Weight of isolated benzoic acid
%recovery
5)
=………………….…………..…g.
=
=……………….……………..…g.
=
Conclusion and Discussion
Page 1 of 2
Questions
1)
Why do we need to put boiling stones into the distillation flask?
2)
Why do we have to acidify the aqueous layer obtained from Part A step 5?
3)
Aniline is a basic compound while nitrobenzene is neutral. They both can dissolve
very well in hexanes. Propose an extraction method for the separation of aniline
from nitrobenzene.
NH 2
Aniline
NO 2
Nitrobenzene
Page 2 of 2
Name
REPORT
Thin Layer and Column
Chromatography
3
Instructor
Date
Group
†
†
BSAC
ISE
PART A: Mobile Phase Determination
Table 1
Ratio of mobile phase
Distance traveled
(EtOAc : n-hexanes)
by solvent (cm)
Benzil (A) (cm)
Benzoin (B) (cm)
Δ Rf
Rf
Distance traveled by
A
B
0:1
1:1
1:2
1:4
From results above, the suitable mobile phase for separation benzil and benzoin is
…………………………………………………………………………………….........................
Reasons:
……………………………………………………………………………………………………...
………………………………………………………………………………………………………
PART B: Separate a mixture of two compounds by column chromatography
Materials and Conditions:
Stationary phase
= ……………..…………….……..
Mobile phase (Eluting solvent)
= ………………..………………...
The length of stationary phase packing
= ………………………..…….(cm)
The amount of benzyl-benzoin mixture
= ……………………………… (g)
(before dissolve with dichloromethane)
Page 1 of 3
Sketches of Thin-layer chromatography plates of fractions eluted from chromatographic column:
Table 2
Eluates
Fraction no.*
Dried weight (g)
Benzil
Benzil + Benzoin
Benzoin
* Combined fractions monitoring by TLC results
Conclusion and Discussion
Page 2 of 3
Melting point (°C)
% recovery
Questions:
1. What will happen if the eluting solvent (mobile phase) is too polar?
2. What changes should be made in order to maintain good chromatographic separation
when the amount of benzil-benzoin mixture increases?
3. Draw the chemical structures of benzil and benzoin then assign the structure with
higher polarity.
Page 3 of 3
Name
REPORT
4
Preparation of
Cyclohexene from
Cyclohexanol
Instructor
Date
Group
†
†
BSAC
ISE
PART A: Preparation of cyclohexene by dehydration of cyclohexanol
Reaction equation:
Weight of cyclohexanol
= ………… g. = ………………… mol
Theoretical yield of cyclohexene = ………… g. = …………….…… mol
Actual yield
= ………… g. = .…………….…… %
PART B: Test of Unsaturation
Observation
Samples
Bromine test
Cyclohexane
Cyclohexene
Page 1 of 2
Permanganate test
Conclusion and Discussion
Questions:
1. Povide a detailed mechanism for the dehydration of cyclohexanol?
2. The products, cyclohexene and water, are removed from the reaction as an azeotrope. What
is an azeotrope?
3. What is the function of anhydrous Na2SO4?
Page 2 of 2
Name
REPORT
Instructor
5
Alkyl Halides
Date
Group
†
†
BSAC
ISE
Data and Observation
Time required to observe precipitation
Reagent
n-butyl
sec-butyl
tert-butyl
n-butyl
bromo
chloride
chloride
chloride
bromide
benzene
1. NaI in acetone (SN2)
@ room
temperature
@ 50 oC
2. AgNO3 in ethanol (SN1)
@ room
temperature
@ 50 oC
Write a representative chemical equation for the fastest-reacting alkyl halide with each
reagent.
1. NaI in acetone
2. AgNO3 in ethanol
Page 1 of 5
3. Comparison between SN1 and SN2 reactions
Test
Alkyl Halide
Nucleophile
Blank
-
-
A
n-butyl chloride
B
tert-butyl chloride
Observation
(color of bromophenol blue)
Chemical equation:
Page 2 of 5
4. Synthesis of tert-butyl chloride from tert-butyl alcohol
OH
H3 C
Cl
+
CH3
CH3
HCl
H3 C
tert-butyl
alcohol
Hydrochloric
acid (conc.)
Density
(g/mL)
0.79
1.19
Conc.
(mol/l)
---
~ 12.0
Name
CH3
CH3
tert-butyl chloride
Mol. Wt.
Volume
(mL)
Theoretical yield
wt. (g)
=……………..g
Mmol
equivalent
Actual yield = …………………………g
% yield
=…………………………..
=…………………………..%
Product Identity Tests (at room temperature)
Reagents
Observation
NaI in Acetone
AgNO3 in Ethanol
Page 3 of 5
Questions
1. Rank the reactivity (from the most reactive to the least) of n-butyl chloride, secbutyl chloride, and tert-butyl chloride with the following reagents. Briefly explain
your answer.
•
NaI in acetone
•
AgNO3 in ethanol
2. In Part 1&2, why do we need to avoid complete evaporation of solvent when
heating the test tube?
3. If a solution of AgNO3 in water is used in Part 2, what would be the functional
group of the product? Write a reaction mechanism to explain your answer.
Page 4 of 5
4. What is the role of bromophenol blue in Part 3?
5. It is not a good idea to synthesize 2-chloro-3,3-dimethylbutane from 3,3-dimethyl2-butanol using the procedure in Part 4. What would be the actual product from
this reaction and what is the mechanism by which it forms? Also, outline an
alternative preparation method for 2-chloro-3,3-dimethylbutane, starting from a
chemical of your choice.
Page 5 of 5
Name
REPORT
Instructor
6
Alcohols and Phenols
Date
Group
†
†
BSAC
Data and Observation
1)
Water solubility
Hydroxyl compound
Soluble (yes, no, or partially)
Ethanol
1-Butanol
2-Butanol
tert-Butanol
Cyclohexanol
Phenol
2)
Alkali solubility
Hydroxyl compound
Soluble (yes or no)
1-Butanol
Cyclohexanol
Phenol
Draw resonance structures that account for high acidity of phenol
Page 1 of 5
ISE
3)
Reaction with metallic sodium
Hydroxyl compound
After addition of
phenolphthalein
Observation
Ethanol
2-Propanol
tert-Butanol
What is the order of reactivity of the three compounds with sodium?
4)
Reaction with ceric nitrate
Hydroxyl compound
Observation
1-Butanol
2-Butanol
tert-Butanol
Phenol
5)
Tests for phenolic compounds
a. Reaction with ferric chloride solution
Hydroxyl compound
Observation
Ethanol
Phenol
Page 2 of 5
b. Reaction with bromine water
Hydroxyl compound
Observation
Ethanol
Phenol
6)
Lucas test
Hydroxyl
compound
Immediately
5 min
30 min
1-Butanol
Cyclohexanol
tert-Butanol
What is the order of reactivity of the three compounds with Lucas reagent?
7)
Oxidation test with sodium dichromate
Hydroxyl compound
Observation
Ethanol
2-Propanol
tert- Butanol
Page 3 of 5
8)
Identification of an unknown alcohol.
Unknown number…………………………………………..
Test
Observation
Implication
Ceric Nitrate
Ferric Chloride
Lucas test
Oxidation reaction
A possible class of unknown alcohol is ………………………………………………………..
Questions
1. What general conclusions can you draw concerning the solubility of alcohols in
water, based on the results from part 1?
2. Which would be less soluble in water, 1-pentanol or 1-heptanol?
Page 4 of 5
3. Write an equation representing the dissolution of phenol in 10% NaOH.
4. From the part 2, is cyclohexanol more or less acidic than phenol? Why?
5. What type of reaction occurred when phenol was treated with bromine water?
6. How could you distinguish chemically between 2-propanol and tert-butanol?
7. How could you distinguish chemically between tert-butanol and phenol?
8. Is it possible that an unknown alcohols will give negative results with both
Lucas and oxidation tests. Why?
Page 5 of 5
Name
REPORT
7
Aromatic ChemistryNitration of Methyl
Benzoate
Instructor
Date
Group
†
†
BSAC
ISE
Weight of methyl benzoate ……………………………………………………………
Weight of product before recrystallization …………………………………………..
% yield calculation:
Weight of product after recrystallization ……………………………………………..
% yield calculation:
% recovery calculation:
TLC result:
Observed melting point:
Page 1 of 2
Discussion:
………………………………………………………………………………………………………
………………………………………………………………………………………………………
………………………………………………………………………………………………………
Conclusion:
………………………………………………………………………………………………………
………………………………………………………………………………………………………
………………………………………………………………………………………………………
Questions
1. Write the mechanism for nitration of methyl benzoate.
2. Indicate two observations suggesting that the synthesized product is not pure.
Page 2 of 2
Name
REPORT
Instructor
8
Aldehydes and Ketones
Date
Group
†
†
BSAC
ISE
In each box, fill in your observation and classify as a positive or negative result.
Unknown
Reagent
Acetaldehyde
Acetone
Benzaldehyde
Glucose
Benzoin
No…………
2,4-DNP
Tollen’s
Benedict’s
Schiff’s
KMnO4
Iodoform
Page 1 of 2
Conclusion and Discussion
………………………………………………………………………………………………………
………………………………………………………………………………………………………
………………………………………………………………………………………………………
………………………………………………………………………………………………………
……………………………………………………………………………………………………
Questions
1. Which compound(s) give positive tests with 2,4-DNP and Tollen’s but negative test
with Schiff’s reagent?
A. CH3COCOCH3
B. CH3CH(OH)CHO
C. CH3COCH(OH)CH3
D. CH3CH(OH)CH(OH)CH3
2. If you are about to make a small kit for testing ‘formalin’ contamination in fresh food
sold in markets, what reagent would you recommend? Also describe the test result if
formalin is present in the food sample.
Page 2 of 2
Name
REPORT
9
Carboxylic Acids and
Their Derivatives
Instructor
Date
Group
†
†
BSAC
Part 1 Synthesis of ester
Starting acid and alcohol number __________________
Weight of the synthesized ester
______
Color of the resulting ester
Scent of the resulting ester
Boiling range
Possible identity of the starting acid and alcohol (based on scent & b.p.)
(Check the correct answer with your instructor)
Write down the chemical equation for the preparation of your ester.
Calculate the theoretical and percentage yields
Page 1 of 3
ISE
Part 2
1. Solubility experiment
water
5% NaOH
5% NaHCO3
Formic acid
Oxalic acid
Benzoic acid
Methyl benzoate
Acetanilide
2. Ferric hydroxamate reaction
observation
Methyl benzoate
Benzoic acid
3. Reaction with Tollens’ and KMnO4 reagents
Tollens’
KMnO4
Formic acid
Acetic acid
Oxalic acid
Benzoic acid
blank
Questions
1. Give a detailed mechanism for the preparation of isoamyl acetate.
Page 2 of 3
2. a) If 0.116 g of a monocarboxylic acid A is required to stoichiometrically react with
0.1 M NaOH 10 mL. Determine the molecular weight of this acid.
b) If 5.8 g of this acid was used for the preparation of methyl ester, how many grams
of the ester should we get?
3. Suppose a preparation of methyl benzoate involved benzoic acid (12.2 g), methanol
(20 g), and conc H2SO4 (2 mL). If methyl benzoate 8 mL (sp. gr. 1.09) was obtained,
determine the theoretical yield and calculate the percentage yield of the reaction.
Page 3 of 3
Name
REPORT
Instructor
10
Oxidation and Reduction
Date
Group
†
†
BSAC
Data and Observation
Part I Oxidation of Benzoin to Benzil
Weight of starting benzoin
_____________________ g
Weight of benzil after crystallization _____________________ g
melting point
_____________________ oC
Theoretical yield (show calculation) _____________________
_____________________
_____________________
Actual yield
_____________________ g
% Yield
_____________________ g
Part II Reduction of benzoin to hydrobenzoin
Weight of starting benzoin
_____________________ g
Weight of hydrobenzoin after crystallization ________________ g
melting point
_____________________ oC
Theoretical yield (show calculation) _____________________
_____________________
_____________________
Actual yield
_____________________ g
% Yield
_____________________ g
Page 1 of 2
ISE
Summary and Discussions
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
Questions
1. Provide a mechanism for conversion of benzoin to hydrobenzoin?
2. Show the relative stereochemistry of all reduction products?
Page 2 of 2
Name
REPORT
Instructor
11
Amines
Date
Group
†
†
BSAC
ISE
1. Basicity testing
1.1 Water solubility
Amine compound
n-butylamine
Solubility (yes, no, partially)
di-n-butylamine
N,N-dimethylaniline
unknown amine
1.2 Indicator test
Amine compound
observed color of Indicator
phenolphthalein bromothymol blue
n-butylamine
aniline
unknown amine
1.3 Salt formation
Amine compound
Observation after react with
6M HCl
6 M NaOH
n-butylamine
aniline
unknown amine
Chemical equation involving salt formations.
Page 1 of 4
pH range of
amine
2. Reaction with bromine in water
Amine compound
Observation after react with
bromine water
n-butylamine
aniline
unknown amine
Chemical equation involving to bromination
3. Reaction with nitrous acid (azo dye)
Amine compound
Observation after react with
nitrous acid
n-butylamine
aniline
below 5oC:
above 5oC:
unknown amine
Result after aniline diazonium reacts with β−naphthol
Write down the involving chemical equation.
Page 2 of 4
4. Hinsberg Test
Amine compound
Observation of Hinsberg test under
basic condition
acidic condition
aniline
N-methylaniline
N,N-dimethylaniline
unknown amine
5. Rimini test, Simon test, modified Rimini test and modified Simon test
Amine compound
Observation
Rimini test
Simon test
n-butylamine
di-n-butylamine
unknown amine
Amine compound
Observation
modified Rimini test modified Simon test
aniline
N-methylaniline
N,N-dimethylaniline
unknown amine
6. Classification of an unknown amine
Unknown number…………….
Check one
† Aliphatic amine
† Aromatic amine
Reason…………………………………………………………………………………………
Check one
† Primary amine
† Secondary amine
† Tertiary amine
Reason…………………………………………………………………………………………
Page 3 of 4
Questions
1. How could you distinguish between 2-aminonaphalene and n-butylamine?
2. Would you expect the product from benzenesulfonyl chloride and ammonia to be
soluble or insoluble in alkaline? Write down the involving chemical equation
3. Technical grade N,N-dimethylaniline contains traces of N-methylaniline and
aniline. Suggest a method for getting rid of these impurities.
Page 4 of 4
Name
REPORT
12
Instructor
Identification of Organic
Compounds
Date
Group
†
†
BSAC
ISE
Part 1 Solubility tests and solubility classes of unknown A to E
3 = soluble
N/A = non-applicable
Litmus
test
Unknown
water
number
U = insoluble
if
soluble
in water
5%
NaOH
5%
NaHCO3
5% HCl
A
B
C
D
E
Page 1 of 3
conc.
H2SO4
Solubility Class
Part 2 Solubility test and determination of functional group of a specific unknown
Unknown Number …………………….
Physical character………………………………………………………………
Solubility tests and solubility class
water
Litmus
test
5%
NaOH
5%
NaHCO3
5% HCl
conc.
H2SO4
Solubility Class
The possible functional groups of this specific unknown are
……………………………………….………………………………………………
Functional group tests
Hypothetical
Functional
Reagent
Observation
Group
Page 2 of 3
Implication
Functional group tests (continued)
Hypothetical
Functional
Reagent
Observation
Group
The functional group of specific unknown:
Discussion
Page 3 of 3
Implication