ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Question
Chapter 21.7D, Problem 21.22P
Interpretation Introduction
Interpretation:
A mechanism corresponding to the basic hydrolysis of benzonitrile to the benzoate ion and ammonia is to be stated.
Concept introduction:
The basic hydrolysis of benzonitrile to the benzoate ion and ammonia comprises three steps. The first step is the addition of hydroxide ion to the carbon of cyano group. The second step is formation of enol tautomer of amide. The third step is the tautomerism (removal and displacement of a proton).
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Chapter 21 Solutions
ORGANIC CHEMISTRY
Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2PCh. 21.4A - Prob. 21.3PCh. 21.4A - Prob. 21.4PCh. 21.5C - Prob. 21.7PCh. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15PCh. 21.7B - Prob. 21.16PCh. 21.7C - Prob. 21.19P
Ch. 21.7C - Prob. 21.20PCh. 21.7C - Prob. 21.21PCh. 21.7D - Prob. 21.22PCh. 21.7D - The mechanism for acidic hydrolysis of a nitrile...Ch. 21.8A - Prob. 21.24PCh. 21.8C - Prob. 21.25PCh. 21.9 - Prob. 21.26PCh. 21.9 - Prob. 21.27PCh. 21.9 - Prob. 21.28PCh. 21.10 - Draw a mechanism for the acylation of anisole by...Ch. 21.10 - Prob. 21.30PCh. 21.11 - Prob. 21.31PCh. 21.11 - Prob. 21.32PCh. 21.12 - Problem 21-33 Propose a mechanism for the...Ch. 21.12 - Suggest the most appropriate reagent for each...Ch. 21.12 - Show how you would synthesize each compound,...Ch. 21.13 - Prob. 21.36PCh. 21.13 - Prob. 21.37PCh. 21.14 - Prob. 21.38PCh. 21.14 - Prob. 21.39PCh. 21.16 - Prob. 21.40PCh. 21.16 - Prob. 21.41PCh. 21 - Prob. 21.42SPCh. 21 - Give appropriate names for the following...Ch. 21 - Predict the major products formed when benzoyl...Ch. 21 - Predict the products of the following reactions....Ch. 21 - Prob. 21.46SPCh. 21 - Prob. 21.47SPCh. 21 - Prob. 21.48SPCh. 21 - Propose mechanisms for the following reactions.Ch. 21 - Prob. 21.51SPCh. 21 - An ether extraction of nutmeg gives large...Ch. 21 - Prob. 21.53SPCh. 21 - Show how you would accomplish the following...Ch. 21 - Prob. 21.55SPCh. 21 - Prob. 21.56SPCh. 21 - Prob. 21.57SPCh. 21 - Prob. 21.58SPCh. 21 - Prob. 21.59SPCh. 21 - Explain this curious result. What does this...Ch. 21 - Prob. 21.61SPCh. 21 - Prob. 21.62SPCh. 21 - Prob. 21.63SPCh. 21 - A chemist was called to an abandoned aspirin...Ch. 21 - Prob. 21.67SPCh. 21 - The IR spectrum, 13ONTVTR spectrum, and 1HNMR...Ch. 21 - Prob. 21.69SPCh. 21 - Prob. 21.70SPCh. 21 - Prob. 21.71SP
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- 18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forwardWhy is methyl salicylate so easily absorbed through the skin?arrow_forwardShow how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forward
- When 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_forwardDraw the structures for the carbonyl compound and amine required to synthesize benzyl methylamine via reductive amination. Lone pairs do not need to be included.arrow_forwardShow how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product b) Benzene m-bromoaniline c) ethylbenzene p-ethylaniline + o-ethylaniline d) benzene p-bromoaniline + o-bromoanilinearrow_forward
- Two reactions occur when sodium hydroxide is added to methyl salicylate. One is immediate and one only occurs with reflux over time. What type of reaction occurs immediately and with which functional group on methyl salicylate does it react? What type of reaction occurs with reflux over time and with which functional group on methyl salicylate does it react?arrow_forwardPropose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.arrow_forwardHow imines and enamines are converted back to carbonyl compounds by hydrolysis with mild acid ?arrow_forward
- Define the Mechanism - Conversion of Carboxylic Acids to Amides with DCCarrow_forwardThe following compound used in perfumery has a violet-like scent. Propose a synthesis of this compound from benzene. 4-Isopropylacetophenonearrow_forward17-35 Suppose that you take a bottle of benzaldehyde (a liquid, bp 179°C) from a shelf and find a white solid in the bottom of the bottle. The solid turns litmus red; that is, it is acidic. Yet aldehydes are neutral compounds. How can you explain these observations?arrow_forward
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