ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 29.60P

Draw the organic products formed in each reaction.

a.Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  1 d. Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  2

b.Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  3 e. Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  4

c.Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  5 f. Chapter 29, Problem 29.60P, 29.60 Draw the organic products formed in each reaction.

		          d. 
		e. 
	 f. 
 , example  6

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification.

Answer to Problem 29.60P

The organic product formed in given reaction is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  1

Explanation of Solution

In the given reaction, the oxygen of carboxyl group takes a proton from an acid. The carbon of carbonyl carbon acts as an electrophile where the attacking of oxygen of alcohol takes place and gives 1, 2-addition. The transfer of proton takes place leads to the elimination of water molecule. In the final step, deprotonation takes place. The corresponding reaction is shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  2

Figure 1

Conclusion

The organic product formed in given reaction is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: Treatment of amine with t-butoxypyrocarbonate in the presence of triethyl amine yields t-butoxy carbonyl group. (Boc)2O is used to protect the amines in the presence of Et3N.

Answer to Problem 29.60P

The organic product formed in given reaction is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  3

Explanation of Solution

The full form of (Boc)2O is t-butoxypyrocarbonate. It protects the amines towards the action of Et3N. The reaction of given compound with (Boc)2O in the presence of Et3N introduces t-butoxy carbonyl group in a product. The reaction is shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  4

Figure 2

Conclusion

The organic product formed in given reaction is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The full form of DCC is dicyclohexylcarbodiimide. It is a dehydrating agent which is used to synthesized amides, nitriles and ketones.

Answer to Problem 29.60P

The organic product formed in given reaction is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  5

Explanation of Solution

As amine are basic in nature and they have tendency to convert carboxylic acid to carboxylate. In the given reaction, carboxylic acid adds to the DCC and forms a good leaving group which displaces by amine in nucleophilic substitution reaction. DCC forms an amide linkage. The corresponding reaction is shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  6

Figure 3

Conclusion

The organic product formed in given reaction is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: Pd-C is reagent which is used in hydrogenation reaction. In the presence of hydrogen gas it reduces alkene to alkane.

Answer to Problem 29.60P

The organic product formed in given reaction is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  7

Explanation of Solution

In the given reaction, the reactant undergoes catalytic reduction in the presence of Pd-C reagent. It reduces ester into alcohol. The corresponding reaction is shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  8

Figure 4

Conclusion

The organic product formed in given reaction is shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The halogenated derivative of acetic acid is TFA. The full form of TFA is trifluoroacetic acid. It is used to break the ester bond in peptide synthesis.

Answer to Problem 29.60P

The organic products formed in given reaction are,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  9

Explanation of Solution

Treatment of given compound with trifluoroacetic acid cleaves the bond I (mark in red color) to form a product. The corresponding reaction is shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  10

Figure 5

Conclusion

The organic product formed in given reaction is shown in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The full form of Fmoc-Cl is fluorenylmethyloxycarbonyl chloride. The molecular formula of Fmoc-Cl is C15H11ClO2. It introduces a group which protects the amine group in organic synthesis.

Answer to Problem 29.60P

The organic product formed in given reaction is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  11

Explanation of Solution

The Fmoc-Cl introduces a group i.e. comF which protects the amine group towards action of sodium carbonate. In the given reaction, treatment of given compound with sodium carbonate in the presence of Fmoc-Cl forms a product with comF group as shown below.

ORGANIC CHEMISTRY, Chapter 29, Problem 29.60P , additional homework tip  12

Figure 6

Conclusion

The organic product formed in given reaction is shown in Figure 6.

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Chapter 29 Solutions

ORGANIC CHEMISTRY

Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13 What alkene is needed to synthesize...Ch. 29 - Problem 29.14 Draw the structure of each peptide....Ch. 29 - Problem 29.15 Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18 Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19 Draw the structure of the...Ch. 29 - Problem 29.20 Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr: a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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