EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 11, Problem 39P
D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C—O bond, rather than the alkyl C—O bond, by studying the hydrolysis of the following ester under basic conditions:
- a. What product contained the 18O label?
- b. What product would have contained the 18O label if the alkyl C—O bond had broken?
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Students have asked these similar questions
3-Methylbutanoic acid, produced by bacteria from leucine, is a component of wine flavor and is responsible for foot odor.Which
alkylating agent(s) should be used for the malonic ester synthesis of 3-methylbutanoic acid?
O
O
O
A Ethyl bromide and methyl bromide
B 2-Bromopropane and methyl bromide
с
D
2-Bromopropane
Methyl bromide, methyl bromide, methyl bromide
E Methyl bromide, malonyl bromide
The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols.
a. Why does the Ritter reaction not work with primary alcohols?
b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.
10. Which of the following compounds does not undergo hydrolysis with
either acid or basic catalysis:
00
H3Cca
CH3CH2ČNH2
CHICOCHCH3
CH3COCH2CH2CH3
B.
CHICCH2CH3
F. None of the molecules shown undergoes hydrolysis.
Chapter 11 Solutions
EBK ESSENTIAL ORGANIC CHEMISTRY
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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