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Chapter 12: Q22-60E (page 354)

The following synthetic routes are incorrect. What is wrong with each?

Short Answer

Expert verified
  1. The reagent path is incorrect.
  2. Aryl halides cannot participate in SN2 reactions.
  3. The product formed is incorrect.

Step by step solution

01

 Step 1: Reaction (a)

The synthetic route for reaction (a) is wrong.

The given reagents are used in this reaction to carry out bromination for the carbonyl compound. Esters do not undergo bromination with the given reagents.

02

Reaction (b)

The synthetic route for reaction (b) is wrong.

In this reaction, an anion forms an anion of a proton from the reactant (diethyl-2-methyl malonate) by the given base.

In the second step, the anion will attack the phenyl bromide, which is impossible. The nucleophilic attack is impossible on aryl halides because of the double bond between carbon and halide.

03

Reaction (c)

The synthetic route for the reaction (c) is wrong.

The correct sequence and the final product for the given reaction is,

Product formed in reaction (c)

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Most popular questions from this chapter

Assume that you are carrying out the base-induced dehydrobromination of 3-Bromo-3-methyl pentane (Section 11-7) to yield an alkene. How could you use IR spectroscopy to tell which of three possible elimination products is formed, if one includes E/Z isomers?

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With:

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(a)

(b)

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