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Chapter 16: Problem 76

Using your roadmaps as a guide, show how to convert (2-bromoethyl) benzene into 2-chloro-1-phenylethanone. Show all reagents and all molecules synthesized along the way.

Short Answer

Expert verified
Answer: The reagents required for this conversion are Sodium Chloride (NaCl), Chromic Acid (H2CrO4), and Sodium Hydroxide (NaOH). The products formed during this process are (2-Chloroethyl)benzene, Sodium Bromide (NaBr), 2-Chloro-1-phenylethanone, Sodium Chromate (NaCrO4), and Water (H2O).

Step by step solution

01

Substitution of Bromine with Chlorine

To convert (2-bromoethyl) benzene to 2-chloroethylbenzene, we will carry out a nucleophilic substitution reaction using Sodium Chloride (NaCl) as our nucleophile. The reaction can be represented as follows: (2-Bromoethyl)benzene + NaCl ⟶ (2-Chloroethyl)benzene + NaBr
02

Oxidation of 2-Chloroethylbenzene to 2-Chloro-1-phenylethanone

In order to convert 2-chloroethylbenzene into 2-chloro-1-phenylethanone, we need to oxidize the ethyl group to a carbonyl group. This can be achieved using the oxidizing agent chromic acid (H2CrO4) in the presence of a base such as sodium hydroxide (NaOH). The reaction can be represented as follows: (2-Chloroethyl)benzene + H2CrO4 + NaOH ⟶ 2-Chloro-1-phenylethanone + NaCrO4 + H2O In conclusion, we have successfully converted (2-bromoethyl) benzen
03

Reagents and molecules synthesized

The necessary reagents for this conversion are: 1. Sodium Chloride (NaCl) - for the nucleophilic substitution reaction 2. Chromic Acid (H2CrO4) - an oxidizing agent to oxidize the ethyl group 3. Sodium Hydroxide (NaOH) - a base to facilitate the oxidation The molecules synthesized during this process are: 1. (2-Chloroethyl)benzene - the intermediate product formed after the nucleophilic substitution reaction 2. Sodium Bromide (NaBr) - a byproduct of the nucleophilic substitution reaction 3. 2-Chloro-1-phenylethanone - the final product 4. Sodium Chromate (NaCrO4) - a byproduct of the oxidation reaction 5. Water (H2O) - a byproduct of the oxidation reaction

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Most popular questions from this chapter

( \(R\) )-Pulegone is converted to \((R)\)-citronellic acid by addition of HCl followed by treatment with \(\mathrm{NaOH}\).

Propose a mechanism to account for the formation of a cyclic acetal from 4-hydroxypentanal and one equivalent of methanol. If the carbonyl oxygen of 4-hydroxypentanal is enriched with oxygen-18, do you predict that the oxygen label appears in the cyclic acetal or in the water?

The base-promoted rearrangement of an \(\alpha\)-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2 -chlorocyclohexanone to cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2 -chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.

The following bicyclic ketone has two \(\alpha\)-carbons and three \(\alpha\)-hydrogens. When this molecule is treated with \(\mathrm{D}_{2} \mathrm{O}\) in the presence of an acid catalyst, only two of the three \(\alpha\)-hydrogens exchange with deuterium. The \(\alpha\)-hydrogen at the bridgehead does not exchange.

Both 1,2 -diols and 1,3 -diols can be protected by treatment with 2-methoxypropene according to the following reaction. (a) Propose a mechanism for the formation of this protected diol. (b) Suggest an experimental procedure by which this protecting group can be removed to regenerate the unprotected diol.
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