Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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Question
Chapter 28.7, Problem 12P
Interpretation Introduction
Interpretation:
Determine the mechanism for the cleavage of β-cyanoethyl protective group by using aqueous ammonia and state the type of occurring reaction.
Concept introduction:
The cleavage of β-cyanoethyl protective group occurs according to the β-elimination mechanism. In β-elimination mechanism, the bond β to the nucleophilic pair of electrons breaks. The elimination reaction involves the breaking of the sigma (σ) bond and the formation of new pie (π) bond. In this process a lone pair electron forms a double bond as the leaving group departs.
Given information:
The cleavage of β-cyanoethyl protective group can be done by aqueous ammonia. The by-product of this reaction is acrylonitrile.
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6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
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1.0
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acid
7. Mild H₂O*
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5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
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(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
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5.1.0 Equiv. LDA
Br
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Chapter 28 Solutions
Organic Chemistry - With Access (Custom)
Ch. 28.1 - Draw the full structure of the DNA dinucleotide...Ch. 28.1 - Draw the full structure of the RNA dinucleotide...Ch. 28.2 - What sequence of bases on one strand of DNA is...Ch. 28.4 - Show how uracil can form strong hydrogen bonds to...Ch. 28.4 - What RNA base sequence is complementary to the...Ch. 28.4 - From what DNA base sequence was the following RNA...Ch. 28.5 - List codon sequences for the following amino...Ch. 28.5 - List anticodon sequences on the tRNAs carrying the...Ch. 28.5 - What amino acid sequence is coded by the following...Ch. 28.5 - What is the base sequence in the original DNA...
Ch. 28.7 - Prob. 11PCh. 28.7 - Prob. 12PCh. 28.SE - Identify the following bases, and tell whether...Ch. 28.SE - Identify the following nucleotide, and tell how it...Ch. 28.SE - Amine bases in nucleic acids can react with...Ch. 28.SE - The final step in DNA synthesis is deprotection by...Ch. 28.SE - The final step in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of a...Ch. 28.SE - One of the steps in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of uridine...Ch. 28.SE - Human brain natriuretic peptide (BNP) is a small...Ch. 28.SE - Human and horse insulin both have two polypeptide...Ch. 28.SE - The DNA of sea urchins contains about 32% A. What...Ch. 28.SE - The codon UAA stops protein synthesis. Why does...Ch. 28.SE - Which of the following base sequences would most...Ch. 28.SE - For what amino acids do the following...Ch. 28.SE - Prob. 27APCh. 28.SE - Prob. 28APCh. 28.SE - Draw the complete structure of the ribonucleotide...Ch. 28.SE - Draw the complete structure of the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - Prob. 35APCh. 28.SE - Show the steps involved in a laboratory synthesis...Ch. 28.SE - Draw the structure of cyclic adenosine...Ch. 28.SE - Prob. 38AP
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