Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
Question
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Chapter 18, Problem 18.27P

(a)

Interpretation Introduction

Interpretation:

Product formed during the reaction of given anhydride with the given reagent has to be shown.

Concept Introduction:

Acid-catalyzed hydrolysis: In presence of strong acid such as H2SO4, ester reacts with water to form the corresponding alcohol and carboxylic acid. It is the reverse of esterification.

(b)

Interpretation Introduction

Interpretation:

Product formed during the reaction of given anhydride with the given reagent has to be shown.

Concept Introduction:

Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.

Saponification: Ester hydrolysis taking place in presence of base such as NaOH or KOH is known as saponification. Ester reacts with hydroxide ion forming carboxylic acid which again reacts with base resulting in the formation of a caboxylate anion.

Acid-catalyzed hydrolysis: In presence of strong acid such as H2SO4, ester reacts with water to form the corresponding alcohol and carboxylic acid. It is the reverse of esterification.

(c)

Interpretation Introduction

Interpretation:

Product formed during the reaction of given anhydride with the given reagent has to be shown.

Concept Introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH4 which provides alcohol.

LAH Reduction: The saturated/unsaturated aldehyde and ketones in the presence of sodium metal in LAH and carbonyl compound produced saturated alcohols. The keto group involves in the reduction process of LAH, this end up reducing to give the alcohols.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of π-bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

(d)

Interpretation Introduction

Interpretation:

Product formed during the reaction of given anhydride with the given reagent has to be shown.

Concept Introduction:

Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.

Saponification: Ester hydrolysis taking place in presence of base such as NaOH or KOH is known as saponification. Ester reacts with hydroxide ion forming carboxylic acid which again reacts with base resulting in the formation of a caboxylate anion.

Acid-catalyzed hydrolysis: In presence of strong acid such as H2SO4, ester reacts with water to form the corresponding alcohol and carboxylic acid. It is the reverse of esterification.

(e)

Interpretation Introduction

Interpretation:

Product formed during the reaction of given anhydride with the given reagent has to be shown.

Concept Introduction:

Reaction of an ester with ammonia or an amine:

Treatment of an ester with ammonia or a primary or secondary amine gives an amide.

The nucleophilic addition of the ammonia or amine to the carbonyl carbon occurs followed by a proton transfer and a tetrahedral addition intermediate is formed. The intermediate can directly alkoxide and lose a proton to the alkoxide to give products.

Organic Chemistry, Chapter 18, Problem 18.27P

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Chapter 18 Solutions

Organic Chemistry

Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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