Organic Chemistry, Books a la Carte Edition (9th Edition)
Organic Chemistry, Books a la Carte Edition (9th Edition)
9th Edition
ISBN: 9780134160382
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24, Problem 24.29SP

(a)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Ninhydrin reacts with alpha amino acids to give resonance stablised anion known as Ruhemann’s purple accompanied by evolution of carbon dioxide. The side chain of amino acid is lost as an aldehyde. This reaction is used to detect amino acids on a wide range of substrates.

(b)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Carboxyl benzyl is used to protect the amine group of amino acids. Its symbol is Cbz. It is used in the synthesis of amides.

(c)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Acetic anhydride is commonly used for acylation of amino acids. All sorts of acylating agents can react with amino group of amino acids. Amino acids contain two major functional groups: the amino group and the carboxylate group.

(d)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Acetic anhydride is commonly used for acylation of amino acids. All sorts of acylating agents can react with amino group of amino acids. Amino acids contain two major functional groups: the amino group and the carboxylate group.

(e)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(f)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(g)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Carboxylic acids react with bromine and phosphorus tribromide to give α-bromo acyl bromide. This intermediate is hydrolysed to give α-bromo acids. The reaction mechanism is acid-catalysed α halogenation. The enol form of the acid acts as a nucleophilic intermediate.

(h)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be stated.

Concept introduction: Carboxylic acids react with bromine and phosphorus tribromide to give α-bromo acyl bromide. This intermediate is hydrolysed to give α-bromo acids. These α-bromo acids react with excess of ammonia to give amino acids.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
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Chapter 24 Solutions

Organic Chemistry, Books a la Carte Edition (9th Edition)

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