Order Substitution and Elimination Reactions

Order Substitution and Elimination Reactions
Order Substitution and Elimination Reactions
1. The main difference between the rate law for an SN2 mechanism and
that for an SN1 mechanism is that the rate law for an SN2 process depends
only on:
(A) The concentration of the substrate and the concentration of the
nucleophile.
(B) The concentration of the nucleophile.
(C) The concentration of the substrate.
(D) The concentration of the solvent.
2. Which of the following is true concerning an SN2 mechanism?
(A) The concentration of the nucleophile is not important.
(B) It is a two-step process.
(C) There is retention of configuration.
(D) Primary alkyl halides react faster than secondary or tertiary alkyl
halides.
3. What is the best explanation of why CH3CH2Cl reacts via an SN2
mechanism faster than CH3CH2CH2CH2Cl does?
(A) The ethyl group leads to less steric interference.
(B) Ethyl chloride has a lower boiling point than butyl chloride.
(C) Ethyl chloride interacts less with the solvent.
(D) The ethyl group stabilizes the intermediate carbocation better.
124. An organic chemist examined a number of reactions involving an SN2
mechanism and found a decrease in the rate with increased size of the
primary alkyl halide. In addition, there was a decrease in the rate with
an increase in the branching on the alkyl halide. What do these facts help
to clarify?
(A) The steric effects on this reaction
(B) The increased stability of larger alkyls
(C) The high reactivity of alkyl halides
(D) The decrease in polarity of larger alkyl halides
125. The monochlorination of methylpropane gives 64% 1-chloro-2-
methylpropane and 36% 2-chloro-2-methylpropane. What is the
approximate selectivity ratio of 3° to 1° in the reaction?
(A) 64:36
(B) 36:64
(C) 1:9
(D) 5:1
52 › McGraw-Hill Education 500 MCAT: Organic Chemistry
126. An organic chemist uses the following reaction to produce the starting
material for another reaction. The reaction takes place in dry ether and
gives one organic product.
2 Li
I
Order Substitution and Elimination Reactions
What is the major product of this reaction?
(A)
Li
(B)
Li
(C)
LiI
(D) Li
I
127. It is possible to form an ether through the reaction of an alkoxide with a
primary alkyl halide. What is the function of the alkoxide in this reaction?
(A) It is an electrophile.
(B) It is a nucleophile.
(C) It is an acid.
(D) It is a catalyst.
128. How many products form in the monochlorination of
2,4-dimethylpentane?
(A) 12
(B) 8
(C) 4
(D) 1
Substitution and Elimination Reactions  53
129. An organic chemist investigates the following reaction:
OH
K2Cr2O7
H2SO4
What is the major product?
(A)
O
OH
(B)
(C) O
(D) OCrO3
54 › McGraw-Hill Education 500 MCAT: Organic Chemistry
130. An organic chemist investigates the following reaction:
OH
K2Cr2O7
H2SO4
What is the major product?
(A)
(B)
O
(C) O
(D)
O
OH
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