(a) Interpretation: The non-feasibility of given reaction is to be explained. Concept Introduction: Primary alcohol reacts with hydrogen bromide to form alkyl halide . The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

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Answer 1

Question

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

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3. a. Use the MS to propose at least two possible molecular formulas. For an unknown compound: 101. 27.0 29.0 41.0 50.0 52.0 55.0 57.0 100 57.5 58.0 58.5 62.0 63.0 64.0 65.0 74.0 40 75.0 76.0 20 20 40 60 80 100 120 140 160 180 200 220 m/z 99.5 68564810898409581251883040 115.0 116.0 77404799 17417M 117.0 12.9 118.0 33.5 119.0 36 133 0 1.2 157.0 2.1 159.0 16 169.0 219 170.0 17 171.0 21.6 172.0 17 181.0 1.3 183.0 197.0 100.0 198.0 200. 784 Relative Intensity 2 2 8 ō (ppm) 6 2

Solve the structure and assign each of the following spectra (IR and C-NMR)

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Answer 2

Question

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

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Answer 3

Question

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

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Answer 4

Question

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

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Answer 5

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

Answer 6

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Answer 7

Chapter 21, Problem 21.52AP

Interpretation Introduction

(a)

Interpretation:

The non-feasibility of given reaction is to be explained.

Concept Introduction:

Primary alcohol reacts with hydrogen bromide to form alkyl halide. The reaction proceeds via carbocation intermediate formation. Bromide ion acts as nucleophile which attacks the primary carbocation to form alkyl halide. As hydrogen bromide is strong acid so there will be considerable amount of bromide ion present in the reaction mixture. Hydrogen cyanide is a weak acid, so it will not dissociate completely to form cyanide and hydrogen ions. The cyanide ion acts as a nucleophile in the reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The non-feasibility of synthesis of half ester of adipic acid is to be explained.

Concept Introduction:

Esterification reaction is a reaction between carboxylic acid and alcohol to form an ester. In the first step, carbonyl oxygen of acid gets protonated, and then the carbocation of acid is formed. In second step, lone pair of oxygen atom of alcohol attacks the carbocation and ester is formed with elimination of water.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The non-feasibility of synthesis of acetic benzoic anhydride is to be explained.

Concept Introduction:

Anhydride is compound containing two carbonyl functional groups, both connected to same oxygen atom. The dehydration of acid gives anhydride. Anhydride can be formed using acid and acyl chloride.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The non-feasibility of saponification of methyl salicylate with one equivalent of NaOH is to be explained.

Concept Introduction:

Saponification reaction is formation of carboxylic acid and alcohol from an ester. The bond between acid and alcohol is cleaved in the presence of base. It is hydration reaction of esters in presence of hydroxide ions.

Answer 14

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

Answer 15

Interpretation Introduction

(e)

Interpretation:

The non-feasibility of de-amidation reaction of cephalosporin derivative is to be explained.

Concept Introduction:

Amide bond is formed when a carboxylic acid and an amine undergoes condensation reaction. In the de-amidation reaction, the amide bond is cleaved to form carboxylic acid and amine. The reaction takes place in the presence of an acid.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

Solution Summary: The author explains the non-feasibility of the reaction of primary alcohol with hydrogen cyanide to form nitrile derivative.

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Chapter 21 Solutions