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Ch. 21 - Carboxylic Acid Derivatives
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 21 - Carboxylic Acid DerivativesProblem 54d
Chapter 21, Problem 54d

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol

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Identify the starting material (ethyl acetate) and the target product (3-methylpentan-3-ol). Ethyl acetate is an ester, and the target compound is a tertiary alcohol. This suggests that the synthesis will involve a Grignard reaction, as Grignard reagents are commonly used to form tertiary alcohols.
Prepare the Grignard reagent needed for the reaction. To form 3-methylpentan-3-ol, the Grignard reagent should be derived from 2-methylpropyl bromide (CH₃)₂CHCH₂Br. React this alkyl halide with magnesium (Mg) in dry ether to form the Grignard reagent (CH₃)₂CHCH₂MgBr.
React the Grignard reagent (CH₃)₂CHCH₂MgBr with ethyl acetate (CH₃COOCH₂CH₃). The Grignard reagent will attack the carbonyl carbon of the ester, leading to the formation of a ketone intermediate (3-methylpentan-2-one).
Add a second equivalent of the Grignard reagent (CH₃)₂CHCH₂MgBr to the ketone intermediate (3-methylpentan-2-one). This will result in the formation of a tertiary alcohol after the addition reaction.
Perform an acidic workup (e.g., using H₃O⁺) to protonate the alkoxide intermediate and obtain the final product, 3-methylpentan-3-ol.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the synthesis of 3-methylpentan-3-ol from ethyl acetate, understanding how nucleophiles can displace groups is crucial for planning the reaction steps.
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Nucleophiles and Electrophiles can react in Substitution Reactions.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles, allowing for the formation of carbon-carbon bonds. In this synthesis, a Grignard reagent can be used to add a carbon chain to the carbonyl carbon of an intermediate, facilitating the conversion of ethyl acetate to the desired alcohol.
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Carbonation of Grignard Reagents

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another, which is often necessary in multi-step syntheses. In the conversion of ethyl acetate to 3-methylpentan-3-ol, it is essential to understand how to manipulate functional groups, such as converting esters to alcohols, to achieve the final product.
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Related Practice
Textbook Question

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents

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Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(c) isobutylamine → N-isobutylformamide

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Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol → isopentyl acetate (banana oil)

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Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile

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Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol

Textbook Question

Grignard reagents add to carbonate esters as they add to other esters.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan®.

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