Consider the following statements in reference to S N 1, S N 2, E1 and E2 reacti
ID: 558386 • Letter: C
Question
Consider the following statements in reference to SN1, SN2, E1 and E2 reactions of alkyl halides. To which mechanism(s), if any, does each statement apply?
a) Involves a carbocation intermediate
b) Is first-order in alkyl halide and first-order in nucleophile
c) Involves inversion of configuration at the site of substitution
d) Involves retention of configuration at the site of substitution
e) Substitution at a stereocenter gives predominantly a racemic product
f) Is first-order in alkyl halide and zero-order in base
g) Is first-order in alkyl halide and first order in base
h) Is greatly accelerated in protic solvents of increasing polarity
i) Rearrangements are common
j) Order of reactivity is 3°> 2° > 1° > methyl
k) Order of reactivity is methyl > 1°> 2° >3°
Explanation / Answer
a) Involves a carbocation intermediate
E1, SN1
b) Is first-order in alkyl halide and first-order in nucleophile
SN2
c) Involves inversion of configuration at the site of substitution
SN2
d) Involves retention of configuration at the site of substitution
SN1
e) Substitution at a stereocenter gives predominantly a racemic product
SN1
f) Is first-order in alkyl halide and zero-order in base
E1
g) Is first-order in alkyl halide and first order in base
E2
h) Is greatly accelerated in protic solvents of increasing polarity
SN1, E1
i) Rearrangements are common
SN1, E1
j) Order of reactivity is 3°> 2° > 1° > methyl
SN1, E1
k) Order of reactivity is methyl > 1°> 2° >3°
SN2