Experimental
The synthesis of caproic acid took place over a 3 week period. The first week
focused on the synthesis of diethyl n-butylmalonate. To begin the synthesis sodium
ethoxide (50.00mL, 0.134 mol) was transferred into a 250 mL round bottom flask
co
Dr. Peter Wipf
Chemistry 0310
A.
Sample Exam - Answer Key
2/9/04
(20 points) Show how each of the following transformations might be achieved:
a)
O SO 2CH3
N aN3
(R) -CH3 CHCH2C H3
N3
( S) -CH3 CHCH2 CH3
b)
CH3
H
Br
CH3 O
H
CH3
1 . K I, a ceto ne
2 . Na C
Abstract
The total synthesis of caproic acid consisted of three main reactions. The starting
material of diethyl malonate was synthesized to diethyl n-butylmalonate with the use of
sodium ethoxide and n-Butylbromide. This reaction gave a 36.87% yield. Key
Maddie Kay
Benzoic Acid
Discussion
Above all, this lab tested and experimented with one of the most important
laboratory techniques used by all chemists extraction. Two different types of extractions
were explored throughout the experiment and many of the
Results
Percent yield was found after each week of the reaction. Table 1 depicts how
percent yield was found.
Table 1: Mass in grams, percent yield of each step of synthesis.
Product of reaction
Calculation using:
Percent Yield
Diethyl n-butylmalonate
Die
Dr. Peter Wipf
Chemistry 0310
Sample Exam II/Answer Key
3/24/04
H. (30 points) Propose a structure for a formula C 10H10O2 that is in agreement with the following
spectroscopic data:
O
H
O
Dr. Peter Wipf
Chemistry 0310
3/24/2004
Name_
SSN_
Signature_
Points [200]_
Exam II
Problem
A
B
C
D
E
F
G
H
Good Luck!
Points
Page 2
CHEM 0310
A.
(20 points) Provide products for the following reactions:
a)
Cl
L iOE t, EtOH
b)
O
E tI
+
DMS O
KO
c)
CH3
H
B
CHM 0330
Sodium Borohydride Reduction: The Conversion of Benzophenone to Diphenylmethanol
Instructor:
March 20th, 2013
Abstract
The goal of the lab was to reduce benzophenone to diphenylmethanol with the use
of the reducing agent sodium borohydride. The p
Dr. Peter Wipf
Chemistry 0310
1/31/2004
Name_
SSN_
Signature_
Points [200]_
Sample Exam
Problem
A
B
C
D
E
F
G
H
Good Luck!
Points
Page 2
CHEM 0310
A.
(20 points) Show how each of the following transformations might be achieved:
a)
N3
O SO 2CH3
(R) -CH3 CH
Dr. Peter Wipf
Chemistry 0310
Quiz II - Solutions
Problem A
(60 points) Predict the major products for the following transformations:
a)
O
H 2 O, O2
cat. PdCl2
cat. CuCl2
b)
I2
no reaction
c)
H
H
Br
Br2
H
Br
H
Problem B (40 points) Give a specific example
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Chapter 3
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Chapter 3
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Chapter 8
Dr. Peter Wipf
Chemistry 0310
A.
Midterm I - Answer Key
(20 points) Draw the product of each of the following reactions:
a)
H
H
NaSMe
Br
SCH3
H
H
b)
MeI
N
I
N
c)
OSO2CH3
(R)-CH3CHCH2CH3
NaN3
N3
(S)-CH3CHCH2CH3
d)
CH3
H
Br
CH3O
H
CH3
1. KI, acetone
2. NaCN
Dr. Peter Wipf
Chemistry 0310
Exam II/Answer Key
4/3/04
A.
(20 points) Propose a structure for a formula C 8H8O3 that is in agreement with the
following spectroscopic data: Vanillin!
B.
(20 points) Give a specific example (no R groups) for (a) an SN1 reac
Dr. Peter Wipf
Chemistry 0310
Quiz I - Solutions
Problem A
(60 points) Draw a typical free energy diagram for (a) an SN2 reaction, (b) an
SN1 reaction. Label all important states along the reaction coordinate.
Problem B (40 points) Give t wo specific exam
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