a) Interpretation: The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R 2 SCN] + . The structure of the product formed is to be given and a mechanism for its formation is to be proposed. Concept introduction: S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction. To give: The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R 2 SCN] + along with the mechanism of its formation.

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Answer 1

Question

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

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Answer 2

Question

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

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Answer 3

Question

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

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Answer 4

Question

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

Expert Solution & Answer

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Answer 5

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

Answer 6

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Answer 7

Chapter 26.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The first step of the reaction shown involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

S atom has two unshared pair of electrons. The nucleophilic attack of an unshared pair of electron present in S on the C of BrCN will displace the bromide ion to yield cyanosulfonium ion. It is a nucleophilic substitution reaction.

To give:

The structure of the product formed in the first step of the reaction shown which involves the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion [R₂SCN]⁺ along with the mechanism of its formation.

Answer 8

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Answer 9

Interpretation Introduction

b)

Interpretation:

The second step of the reaction shown is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product. The structure of the product formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The internal nucleophilc attack of the unshared pair of electrons on the sulfonium ion can lead to the formation of a five membered ring product.

To give:

The structure of the product formed in the second step of the reaction shown which is an internal S_N² reaction, in which the carbonyl oxygen of methionine residue displaces the positively charged sulfur group to form a five membered ring product and a mechanism for its formation.

Answer 10

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Answer 11

Interpretation Introduction

c)

Interpretation:

The third step of the reaction given is a hydrolysis reaction to split the peptide chain to yield a lactone. The structure of the lactone ring formed is to be given and a mechanism for its formation is to be proposed.

Concept introduction:

The imine derivative (CH=NH) when hydrolyzed with aqueous acids breaks to give a carbonyl compound and an amino derivative as products.

To give:

The structure of the lactone ring formed during the hydrolysis of the peptide chain and a mechanism for its formation.

Answer 12

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

Answer 13

Interpretation Introduction

d)

Interpretation:

The final step of the reaction given is a hydrolysis of the lactone to give the product. A mechanism for this hydrolysis reaction is to be proposed.

Concept introduction:

Lactones upon hydrolysis give hydroxy acids as products.

To propose:

A mechanism for the hydrolysis of the lactone to give the product.

Answer 14

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Answer 15

Expert Solution & Answer

Answer 16

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Answer 17

Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2P Ch. 26.1 - Prob. 3P Ch. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7P Ch. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P

Solution Summary: The author explains the nucleophilic substitution of the S atom on the methionine side chain with BrCN to give cyanosulfonium ion.

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