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Chapter 16: Problem 48

If the Favorskii rearrangement of 2-chlorocyclohexanone is carried out using sodium ethoxide in ethanol, the product is ethyl cyclopentanecarboxylate.

Short Answer

Expert verified
Question: Briefly outline the steps involved in the Favorskii rearrangement of 2-chlorocyclohexanone and sodium ethoxide to produce ethyl cyclopentanecarboxylate. Answer: The Favorskii rearrangement involves the following steps: 1. Nucleophilic attack of ethoxide ion on 2-chlorocyclohexanone. 2. Formation of a tetrahedral intermediate. 3. Migration of the chlorine atom to form a cyclic intermediate. 4. Ring contraction and chloride anion departure. 5. Protonation of the negatively charged oxygen atom to form ethyl cyclopentanecarboxylate as the final product.

Step by step solution

01

Understand the reactants and conditions

The given reactants are 2-chlorocyclohexanone, which is a cyclohexanone with a chlorine atom attached to the 2-position, and sodium ethoxide (NaOEt), which is a strong base and nucleophile in this reaction. The solvent used is ethanol.
02

Nucleophilic attack on 2-chlorocyclohexanone

The reaction occurs by the nucleophilic attack of the ethoxide ion (EtO^-) on the carbonyl carbon of 2-chlorocyclohexanone. This step generates a tetrahedral intermediate and the negative charge residing on the oxygen atom.
03

Formation of an intermediate

The next step involves the migration of the chlorine atom from the 2-position to the initially negatively charged oxygen atom, leading to a cyclic intermediate. The cyclic intermediate consists of an ester-like moiety with a chloride anion as a leaving group.
04

Ring contraction and chloride anion departure

In this step, the negatively charged oxygen atom attacks the neighboring carbon atom bonded to the chlorine. The chloride anion (Cl^-) departs as a leaving group, causing a ring contraction from a six-membered cyclohexanone to a five-membered cyclopentanone.
05

Formation of the final product, ethyl cyclopentanecarboxylate

The last step involves the protonation of the negatively charged oxygen atom (from the EtO^- of sodium ethoxide) to form the final product, ethyl cyclopentanecarboxylate. This occurs by transferring a hydrogen (proton) from ethanol to the negatively charged oxygen atom in the cyclopentanone ring.

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Most popular questions from this chapter

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?

Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol

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.

Using your roadmaps as a guide, show how to convert 1-butanol into racemic 4-octanol. You must use 1-butanol as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.

Using your roadmaps as a guide, show how to convert acetaldehyde into racemic 3-hydroxybutanal. You must use acetaldehyde as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
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