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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Part II. Given two isomers: 2-methylpentane (A) and 2,2-dimethyl butane (B) answer the following: (a) match structures of isomers given their mass spectra below (spectra A and spectra B) (b) Draw the fragments given the following prominent peaks from each spectrum: Spectra A m/2 =43 and 1/2-57 spectra B m/2 = 43 (c) why is 1/2=57 peak in spectrum A more intense compared to the same peak in spectrum B. Relative abundance Relative abundance 100 A 50 29 29 0 10 -0 -0 100 B 50 720 30 41 43 57 71 4-0 40 50 60 70 m/z 43 57 8-0 m/z = 86 M 90 100 71 m/z = 86 M -O 0 10 20 30 40 50 60 70 80 -88 m/z 90 100

Part IV. C6H5 CH2CH2OH is an aromatic compound which was subjected to Electron Ionization - mass spectrometry (El-MS) analysis. Prominent m/2 values: m/2 = 104 and m/2 = 9) was obtained. Draw the structures of these fragments.

For each reaction shown below follow the curved arrows to complete each equationby showing the structure of the products. Identify the acid, the base, the conjugated acid andconjugated base. Consutl the pKa table and choose the direciton theequilibrium goes. However show the curved arrows. Please explain if possible.

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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