291B SP16 E1A Key

Chem 291B
Spring 2016
Exam 1 Answer Key

100 points
Print Last Name: _____________
Question
1
2
3
4
5
6
7
8
9
Total
points
10
10
10
10
15
15
10
10
10
100
score
60 min
Print First Name: _________________
H
2.1
Li
1.0
Na
0.9
K
0.8
Rb
0.8
Electronegativity values
Be
1.5
Mg
1.2
Ca
1.0
Sr
1.0
B
2.0
Al
1.5
Ga
1.6
In
1.7
C
2.5
Si
1.8
Ge
1.8
Sn
1.8
N
3.0
P
2.1
As
2.0
Sb
1.9
O
3.5
S
2.5
Se
2.4
Te
2.1
He
F
4.0
Cl
3.0l
Br
2.8
I
2.5
Ne
Ar
Kr
Xe
Question1:[10 pts] Show the intermediate and product(s) formed in the following reaction.
(a) Via an SN2 mechanism. (b) via an SN1 mechanism. Pay attention to stereochemistry.
Clearly show the stereochemistry and determine if they are R or S configuration.
a. SN2
b. SN1 mechanism
mechanism
Question 2: [10 pts] The initial rates of the following elimination were measured under different concentrations of the
substrate and base; the data are tabulated below.
Do the data suggest a E1 or E2 reaction? Why? Explain.

Ans: The kinetic data indicates that the rate does not depend on the concentration of nucleophile. Therefore, E!mechanism
Write an equation for the rate law. => Rate = k [R-OCH3]
Question 3: [10 pts] An example of a protic solvent is (circle one) acetone or ethanol.
For each of the following pairs of species, circle the stronger nucleophile in acetone?
Explain why other is a weak nucleophile.

Ans_ electrons on A delocalized by resonance
Explain why other is a weak nucleophile

Ans: In aprotic solvents B is poor nucleophile.
Question #4. For each of the following pairs of species, which is the stronger nucleophile in ethanol? Explain.
Explain why other is a weak nucleophile
ANS: No charge on O-H
Explain why other is a weak nucleophile.

ANS: Protic solvebt solvates the -OH
Exam 1 Answer Key

Question #5 (15 points)
a.
b.
c.
d.
e.
(CH3)3CO- is a (circle one) strong bulky base or weak bulky base

TsO- is (circle one) an excellent leaving group or a poor leaving group.
DMSO is an aprotic solvent and favors (circle one) SN2 and E2 or SN1 and E1
High temperature favors (circle one) substitution or elimination.
For the following reaction, provide a complete, detailed mechanism and predict the product(s).
f.
g.
h.
i.
Ethanol is a (corcle one) strong or weak nucleophile.

Ethanol is a (circle one) weak base or strong base.
Ethanol a protic solvent favors (circle one) SN1 and E1 or SN2 and E2 .
A tertiary carbocation is (circle one) more stable or less stable than a secondary carbocation.
For the following reaction, provide a complete, detailed mechanism and predict the product(s).
Question # 6 (15 pts)
a.
b.
c.
d.
Fill in the blanks.

The following reaction is a (SN1 or SN2) => Bimolecular Nucleophilic Substitution reaction.
In the following reaction you get (inversion of stereochemistry or racemic mixture)
OCH3 is a strong or weak nucleophile? => Strong
CH3OH is a (strong or weak) base? =>weak
Suggest how the following reactions could be carried out, focusing in particular on the identity of the nucleophile and the
choice of solvent.
e. The following reaction is a (SN1 or SN2) reaction? => Unimolecular Nucleophilic Substitution
f. In the following reaction you get (inversion of stereochemistry or racemic mixture) => Racemic Mixture
Exam 1 Answer Key

Question #7: [10 pts] Consider the following reactions and figure out whether the predominant mechanism is SN1, SN2,
E1 or E2. Then write structure of the product(s) in each case. Clearly show the stereo chemical changes.
a.
Ans: E1 is favored, but no carbocation rearrangement is feasible. However, cis and trans isomers are formed.
b.
Question #8: [10 pts] DMSO is a (circle one) (a) polar protic solvent or (b) polar aprotic solvent.
Explain the following reaction sequence and determine the structures for A and B
Ans: The first reaction to produce A is an SN2 reaction. The secondary

benzylic carbon in the presence of a strong nucleophile, in an aprotic
solvent (DMSO) favors SN2 with inversion of stereochemistry. The
second reaction to produce B first involves a proton transfer to
deprotonate the alcohol using NaH Which produces a strongly
nucleophilic alkoxide anion, and then an SN2 follows.
Question #9 [10 pts]

Determine if the following statements are TRUE or FALSE
a. TRUE
The rate of an SN2 reaction is directly proportional to the concentration of the

nucleophile. Whereas the rate of an SN1 reaction is independent of the
concentration of nucleophile.
b. TRUE
SN2 reactions require back-side attack and result in inversion of configuration
c. TRUE
The reaction of a carboxylic acid with diazomethane (CH2N2) yields a methyl

ester.
In Williamson ether synthesis an alkyl halide is treated with a salt of of an
alkoxide.
d. TRUE
e. TRUE
Epoxides can undergo SN2 reactions in neutral or basic solution due to the
relief of ring strain.
f.
Under acidic condition, a nucleophile attacks an epoxide at a more highly alkyl

substituted carbon.
TRUE
g. TRUE
The major product of Hofmann elimination is the anti Zatsev product
h. TRUE
An E2 reaction favors an antiperiplanar conformation of the proton and the

leaving group.
i.
TRUE _
In an electrophilic addition of a Bronsted acid to an alkene, the rate

determining step 1: addition of H+ electrophile
j.
TRUE _
The addition of hydrogen bromide to an alkene favors the production which the
proton adds to the Alkene carbon initially bonded to greater number of
hydrogen atoms.
-: END :-

291B SP16 E1A Key

Uploaded by

Copyright:

Available Formats

291B SP16 E1A Key

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

291B SP16 E1A Key

Uploaded by

Copyright:

Available Formats

Chem 291B

Exam 1 Answer Key

Print Last Name: _____________

Print First Name: _________________

Do the data suggest a E1 or E2 reaction? Why? Explain.

Explain why other is a weak nucleophile.

Explain why other is a weak nucleophile

ANS: No charge on O-H

Explain why other is a weak nucleophile.

Exam 1 Answer Key

(CH3)3CO- is a (circle one) strong bulky base or weak bulky base

Ethanol is a (corcle one) strong or weak nucleophile.

Question # 6 (15 pts)

Fill in the blanks.

Exam 1 Answer Key

Ans: The first reaction to produce A is an SN2 reaction. The secondary

Question #9 [10 pts]

The rate of an SN2 reaction is directly proportional to the concentration of the

SN2 reactions require back-side attack and result in inversion of configuration

The reaction of a carboxylic acid with diazomethane (CH2N2) yields a methyl

Under acidic condition, a nucleophile attacks an epoxide at a more highly alkyl

The major product of Hofmann elimination is the anti Zatsev product

An E2 reaction favors an antiperiplanar conformation of the proton and the

In an electrophilic addition of a Bronsted acid to an alkene, the rate

You might also like