EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Question
Chapter 15.12, Problem 35P
Interpretation Introduction
Interpretation:
The mechanism has to be written for the reaction of an amide with an alcohol in presence of an acid catalyst to give ester as a product.
Concept introduction:
The general reaction of an amide with an alcohol does not give a product. As amides are least reactive
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Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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- Write a general reaction showing the preparation of an ester.arrow_forwardDraw the all the reactants and products involved in a condensation reaction between propanoic acid and ethanamine. Make sure to include the catalyst needed and any secondary products that would form.arrow_forwardWhat is the class of organic compound that is produced when a carboxylic acid derivative undergoes hydrolysis? Carboxylic acid Alcohol Ester Acid Anhydridearrow_forward
- When reacting an acid halide with amines, it is necessary to use at least two moles of the amine because: A) Acid halides are so unreactive that two moles of the attacking nucleophile are needed B) Using one mole of the amine leads to a neutralization reaction between the two reactants C) Excess amine is needed to react with the hydrohalic acid produced D) The second mole of amine is needed for deprotonation.arrow_forwardWhy is aqueous ammonia used in a reaction with an ester to produce an amide and alcohol? Why not use alcoholic ammonia?arrow_forwardDraw the products of acid–base reactions of aminesarrow_forward
- Many substitution reactions are initiated by electrostatic attraction between reactants. Show where this attraction arises in the formation of an amide from an amine and an ester.arrow_forwardWhat is the product when Methyl phenylacetate reacts with NH3 and ether in order to form amide?arrow_forwardWhat is the product when you synthesize methyl salicylate by the process of esterification?arrow_forward
- Which of the following compounds would have the lowest boiling point of the group? O heptanoic acid ethanoic acid butanoic acid decanoic acid cannot be determined from the information givenarrow_forwardTo synthesize the ester called methyl ethanoate, the following alcohol and carboxylic acid can be mixed in the presence of an acid catalyst. methanol and methanoic acid ethanol and ethanoic acid propanol and ethanoic acid methanol and ethanoic acidarrow_forwardCompare and contrast acid hydrolysis and base hydrolysis of carboxylic acid derivatives.arrow_forward
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