Indietro
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblema 22a,b
What is the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ion?
a.
b.
Problema 22c
What is the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ion?
c.
Problema 23a
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
a.
Problema 23b
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
b.
Problema 23c,d
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
c.
d.
Problema 23e
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
e.
Problema 23f
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
f.
Problema 24a,b
Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?
a.
b.
Problema 24c,d
Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?
c.
d.
Problema 25a,b
Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?
a.
b.
Problema 25c,d
Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?
c.
d.
Problema 26
Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methanol. Draw the structures of the alkenes and rank them according to the amount that would be formed.
Problema 27
If 2-fluoropentane could undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.
Problema 28a,b
Which of the following compounds would react faster in an
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a. E1 reaction?
b. E2 reaction?
Problema 29
Propose a mechanism for the following reaction:
Problema 30a,b
For each of the following reactions, (1) decide whether an E2 or an E1 occurs, and (2) draw the major elimination product:
a.
b.
Problema 33(1)
a. What is the major product obtained when each of the following compounds undergoes an E2 reaction with methoxide ion? Show the configuration of the product.
b. Does the product obtained depend on whether you start with the R or S enantiomer of the reactant?
1.
Problema 33(3)
a. What is the major product obtained when each of the following compounds undergoes an E2 reaction with methoxide ion? Show the configuration of the product.
b. Does the product obtained depend on whether you start with the R or S enantiomer of the reactant?
3.
Problema 35a
What is the major product formed when the following compounds undergo an E1 reaction?
a.
Problema 35b
What is the major product formed when the following compounds undergo an E1 reaction?
b.
Problema 35c
What is the major product formed when the following compounds undergo an E1 reaction?
c.
Problema 36
Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?
Problema 37
Which isomer reacts more rapidly in an E2 reaction: cis-1-bromo-4-tert-butylcyclohexane or trans-1-bromo-4-tert-butylcyclohexane? Explain your answer.
Problema 38a
Draw the substitution and elimination products for the following reactions, showing the configuration of each product:
a. trans-1-chloro-2-methylcyclohexane + CH3O−
Problema 38b
Draw the substitution and elimination products for the following reactions, showing the configuration of each product:
b. cis-1-chloro-2-methylcyclohexane + CH3O−
Problema 38c,d
Draw the substitution and elimination products for the following reactions, showing the configuration of each product:
c. 1-chloro-1-methylcyclohexane + CH3O−
d. 1-chloro-1-methylcyclohexane + CH3OH
Problema 39a
Which reacts faster in an SN2 reaction?
Problema 39b
Which reacts faster in an E1 reaction?
Problema 39c
Which reacts faster in an SN1 reaction?
Problema 40
You were told in [SECTION 7.11] that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.
