Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Chapter 21, Problem 21.45SP
Predict the products of the following reactions.
- a. phenol + acetic anhydride
- b. phenol + acetic formic anhydride
- c. aniline + phthalic anhydride
- d. anisole + succinic anhydride and aluminum chloride
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2) Another method for the above reaction starts with 4-aminophenol hydrochloride (the conjugate acid of 4-aminophenol). The treatment of this the hydrochloride salt with sodium ethanoate (acetate) buffer produces 4-aminophenol which is then able to react with ethanoic anhydride as per our method.
i. Why is 4-aminophenol hydrochloride not suitable for direct reaction with ethanoic anhydride?
ii. Draw a mechanism (i.e. curly arrows) showing the deprotonation of 4-aminophenol hydrochloride by sodium ethanoate to form 4-aminophenol (the free base).
(a) Account for the following :(i) Cl – CH2COOH is a stronger acid than CH3COOH.(ii) Carboxylic acids do not give reactions of carbonyl group.(b) Write the chemical equations to illustrate the following name reactions:(i) Rosenmund reduction           (ii) Cannizzaro’s reaction(c) Out of CH3CH2 – CO – CH2 – CH3 and CH3CH2 – CH2 – CO – CH3, which gives iodoform test?
One possible side-reaction of this experiment is biphenyl, explain how it can be formed. Here is the oringial reaction
bromobenzene   ----->magnesium.       product is benze ring with MgBr attached to ring
Chapter 21 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
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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