Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 17, Problem 3LGP
Interpretation Introduction
Interpretation:
The details of the mechanism for the reaction between mixed anhydride and Z-Ala-Leu, and how carbon dioxide and ethanol are formed in the mechanisms are to be discussed.
Concept introduction:
The reaction between nucleophile and acyl compounds is called nucleophilic acyl substitution.
Nucleophilic acyl substitution describe a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile—such as an alcohol, amine, or enolate—displaces the leaving group of an acyl derivative—such as an acid halide, anhydride, or ester.
A mixed anhydride is a
Acid chlorides react with
The carboxylic acid is converted into acid chlorides in the presence of thionyl chloride.
Decarboxylation is the loss of carbon dioxide.
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Students have asked these similar questions
Chlorophyll, heme, vitamin B12, and a host of other substances are synthesized from porphobilinogen, which is itself formed from the condensation of two molecules of 5-aminolevulinate. The two 5-aminolevulinates are bound to lysine (Lys) residues in the enzyme, one in the
enamine form and the other in the imine form. Condensation is thought to occur via a several step process, one of which is shown below.
ÇO2
ÇO2
CO2
+
NH3
NH3
H
H3N
5-aminolevulinate
(enamine form)
5-aminolevulinate
(imine form)
Porphobilinogen
Draw curved arrows to illustrate the movement of electrons in this step of the reaction.
Arrow-pushing Instructions
CO2
CO2
CO2
CO2
:B
BH*
H-A
H3N
H3Ņ
Analyze the mechanism of each rearrangement and list their similarities.
(a) Predict the product of the reaction of KOH with 1-amino propane.
(b) Predict the product of a deprotonated ethanol (an “ethanolate anion", O-CH2-CH3)
with phenol (hydroxybenzene).
(c) Predict the product of propanoic acid with deprotonated ethanol (an “ethanolate
anion", O-CH2-CH3).
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Practice Problem 17.1 Give an IUPAC systematic...Ch. 17 - Prob. 2PPCh. 17 - Practice Problem 17.3 Write structural formulas...Ch. 17 - Practice Problem 17.4
Show how each of the...Ch. 17 - Practice Problem 17.5
Show how you could prepare...Ch. 17 - Practice Problem 17.6
(a) Which of the carboxylic...Ch. 17 - Prob. 7PPCh. 17 - Prob. 8PPCh. 17 - Practice Problem 17.9
Esters can also be...Ch. 17 - Prob. 10PP
Ch. 17 - Prob. 11PPCh. 17 - Practice Problem 17.12
What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 14PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 17PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 19PCh. 17 - Prob. 20PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 22PCh. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 30PCh. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 46PCh. 17 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - Prob. 51PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGP
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