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Chapter 18: Q12P (page 581)

Predict the major product of each of the following reactions:

Short Answer

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Answer

Step by step solution

01

Step-by-Step SolutionStep 1: Reaction of epoxides (Ring-opening)

The epoxide ring is opened by a reaction with acid (HX) in ether, and the substitution pattern of the carbons in the epoxide ring tells where the ring-opening reaction occurs. The more hindered carbon (tertiary) is attacked from the backside, and cleavage occurs.

02

The major product of the reaction in (a)

  1. The ring-opening reaction in acid-catalyzed occurs at that carbon which is more hindered if one of the epoxide carbons is tertiary. In this reaction, the marked carbon is tertiary because two methyl groups are attached. The major product formed is,

Ring-opening reaction

03

The major product of the reaction in (b)

b. In this reaction, the tertiary carbon of the epoxide ring is marked by the arrow. The ring-opening reaction takes place, and the major product formed is shown below,


Ring-opening reaction

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Most popular questions from this chapter

Predict the product(s) and provide the mechanism for each reaction below. What do the mechanisms have in common?

a.

b.

c.

d.

Rank the following halides in order of their reactivity in Williamson synthesis:

  1. Bromoethane, 2-bromopropane, bromobenzene
  2. Chloroethane, bromoethane, 1-iodopropene

Treatment of trans-2-chlorocyclohexanol with NaOH yields 1,2-epoxycyclohexane,but reaction of the cis isomer under the same conditionsyields cyclohexanone. Propose mechanisms for both reactions, andexplain why the different results are obtained.

We saw in section 17-4 that ketones react withNaBH4 to yield alcohols. We鈥檒l also see in section 22-3 that ketones react withBr2 to yield 伪-bromo ketones. Perhaps surprisingly, treatment withNaBH4 of the伪 -bromo ketone from acetophenone yields an epoxide rather than a bromo alcohol. Show the structure of the epoxide, and explain its formation.

Acetophenone An 伪-bromo ketone

How could you prepare benzyl phenyl ether from benzene and phenol? More than one step is required.
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