Assignment #6
CHEM201
Name___________________________________
Student #: _________________________________________
Due Date: _______________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the
question.
1) What is the nucleophile in the reaction shown below?
A) I
B) II
C) III
D) IV
E) V
2) Which of the following alkyl halides gives the slowest SN2 reaction?
A)
B)
C) CH3CH2Cl
D)
E)
3) Which of the following is the strongest nucleophile in an aqueous
solution?
A) BrB) HOC) ID) FE) Cl-
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4) Which of the following is the best leaving group?
B) FC) ID) HOA) Br-
E) Cl-
5) Which of the following species is the least nucleophilic?
A) (CH3)3N
B) CNC) H2O
D) (CH3)3COE) BF3
6) Assuming no other changes, what is the effect of doubling only the
concentration of the nucleophile in the reaction below?
A) doubles the rate
B) quadruples the rate
C) rate is halve
D) no change
E) triples the rate
7) Which of the following carbocations does not rearrange?
A)
B)
C) CH3CH2+CHCH3
D)
E) all the above
8) Which of the following solvents is aprotic?
A) CH3CH2OCH2CH3
B)
C) CH3CH2CH2NH2
D) CH3CH2NHCH3
E) CH3CH2OH
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SHORT ANSWER. Write the word or phrase that best completes each statement or answers the
question.
9) Rank the species below in order of increasing nucleophilicity in
protic solvents: CH3CO2- , CH3S- , HO- , H2O.
10) Provide the structure of the major organic product which results
when (S)-2-iodopentane is treated with KCN in DMF.
11) Provide the structure of the major organic product of the
following reaction.
12) Provide the major organic product(s) in the reaction below.
13) Provide the structure of the major organic product in the
following reaction.
14) Provide the major organic product of the reaction below and a
detailed, stepwise mechanism which accounts for its formation.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the
question.
15) How many distinct alkene products are possible when the alkyl iodide
below undergoes E2 elimination?
A) 1
B) 2
C) 3
D) 4
E) 5
16) Which of the alkyl chlorides listed below undergoes
dehydrohalogenation in the presence of a strong base to give 2-pentene
as the only alkene product?
A) 2-chloropentane
B) 1-chloropentane
C) 1-chloro-3-methylbutane
D) 1-chloro-2-methylbutane
E) 3-chloropentane
17) Which of the following alkyl halides forms the most stable carbocation
when it undergoes an E1 reaction?
A) I
B) II
C) III
D) IV
E) V
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18) Predict the two most likely mechanisms for the reaction of 2-iodohexane
with sodium ethoxide.
A) SN2 and E2
B) SN2 and SN1
C) E1 and E2
D) E1 and SN1
E) E2 and SN1
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the
question.
19) Provide the structure of the major organic product of the
following reaction.
20) Draw all likely alkene products in the following reaction and
circle the product you expect to predominate.
21) Supply the missing alkyl halide reactant in the elimination
reactions shown below.
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22) What reaction mechanism predominates when 1-bromo-1propylcyclopentane is treated with sodium methoxide in
methanol? (DO NOT DRAW THE MECHANISM)
23) Show the best way to prepare CH3OCH(CH3)2 by an SN2
reaction.
24) When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one
of the products which results is shown below. Provide a detailed,
stepwise mechanism for the production of this compound, and give
the name of the mechanism by which it is produced.
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