6.22: Additional Exercises
- Page ID
- 182921
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7-1 Predict which compound in each pair would undergo the SN2 reaction faster.
a) or
b) or
c) or
d) or
7-2 Predict the products of these nucleophilic substitution reactions, including stereochemistry when appropriate.
a)
b)
c)
d)
7-3 Show how each compound might be synthesized using SN2 reaction.
a)
b)
c)
7-4 Show 2 ways to synthesize the ether below using SN2 reaction
7-5 Of the two ways of synthesizing the compound in previous question (7-4), which one would be the most efficient? Why? Show the mechanism of the reaction as part of your explanation.
7-6 Arrange the compounds below in increasing order of nucleophilicity.
H2O; NH2-; CH3O-; CH3CH2O-
SN1
7-7 List the following carbocations in order of increasing stability.
7-8 Give the solvolysis product expected when the compound is heated in methanol.
a)
b)
c)
d)
7-9 Predict with compound in each pair will undergo an SN1 reaction more quickly.
a) or
b) or
c) or
d) or
7-10 Show how the following carbocations would rearrange to become more stable. Draw the mechanism of the rearrangement.
a)
b)
c)
d)
SN2 vs SN1
7-11 Predict whether each compound below would be more likely to undergo a SN2 or SN1 reaction.
a)
b)
c)
d)
7-12 Predict the product of the following reactions.
a)
b)
c)
d)
7-13 Show how each compound may be synthesized using nucleophilic substitution reactions.
a)
b)
c)
d)
e)
f)
g)
E2 vs E1
7-14 Predict the major products of the following reactions.
a)
b)
c)
7-15 Draw the expected major product when each of the following compounds is treated with hydroxide to give an E2 reaction.
a)
b)
c)
7-16 Predict all the elimination products of the following reactions and label the major product.
a)
b)
c)
d)
Substitution vs Elimination
7-17 Identify the function of the following reagents. The reagents will be a strong/weak nucleophile and/or a strong/weak base.
a) Cl-
b) NaH
c) t-BuO-
d) OH-
e) H2O
f) HS-
g) MeOH
7-18 Identify which mechanism the following reactions would undergo.
a)
b)
c)
d)
e)
7-19 Identify all the products of the following reactions and specify the major product.
a)
b)
c)
d)
e)
7-20 The following reaction yields five different products. Give the mechanisms for how each is formed.