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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 54e,f
Chapter 21, Problem 54e,f

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

Verified step by step guidance
1
Step 1: For the conversion of cyclohexylamine to N-cyclohexylacetamide, start by recognizing that this is an acylation reaction. Cyclohexylamine (R-NH2) reacts with an acyl chloride (R'-COCl) to form an amide. Choose acetyl chloride (CH3COCl) as the acylating agent.
Step 2: Mix cyclohexylamine with acetyl chloride in the presence of a base like pyridine or triethylamine. The base neutralizes the HCl byproduct formed during the reaction, ensuring smooth conversion to N-cyclohexylacetamide.
Step 3: For the conversion of bromocyclohexane to dicyclohexylmethanol, recognize that this involves a Grignard reaction. First, convert bromocyclohexane to cyclohexylmagnesium bromide by reacting it with magnesium metal in dry ether.
Step 4: React cyclohexylmagnesium bromide with cyclohexanone (C6H10O). The Grignard reagent adds to the carbonyl group of cyclohexanone, forming an intermediate alkoxide.
Step 5: Perform an acidic workup (e.g., using dilute HCl or water) to protonate the alkoxide intermediate, yielding dicyclohexylmethanol as the final product.

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Key Concepts

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

Amine Reactivity

Cyclohexylamine is a primary amine that can undergo acylation to form N-cyclohexylacetamide. This reaction involves the nucleophilic attack of the amine on an acyl chloride or anhydride, leading to the formation of an amide bond. Understanding the reactivity of amines is crucial for predicting the products of such transformations.
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Bromination and Nucleophilic Substitution

Bromocyclohexane contains a bromine atom that can be replaced through nucleophilic substitution reactions. In the synthesis of dicyclohexylmethanol, the bromine can be displaced by a nucleophile, such as a cyclohexyl anion, followed by reduction to form the alcohol. Familiarity with substitution mechanisms is essential for planning multi-step syntheses.
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Nucleophiles and Electrophiles can react in Substitution Reactions.

Reduction Reactions

Reduction reactions are key in organic synthesis, particularly when converting carbonyl compounds to alcohols. In the case of dicyclohexylmethanol, a carbonyl intermediate formed from the nucleophilic substitution can be reduced using reagents like lithium aluminum hydride or sodium borohydride. Understanding reduction mechanisms is vital for completing the synthesis effectively.
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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.

(d) ethyl acetate → 3-methylpentan-3-ol

543
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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.

(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile

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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. Also show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin® insecticide.

743
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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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