Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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Chapter 22.SE, Problem 34MP
Amino acids can be prepared by reaction of
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What is the order of increasing acidity for the following compounds? (least to most) [2 ONLY]
A.
COOH
COOH
COOH
COOH
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a.
IV, I, III, II
b.
III, II, I, IV
с.
II, III, I, IV
d. III, II, IV, I
slingoros
CH3
IV
woled noise biz
With this, please answer the following questions:
1.) draw the structure of the electrophilic intermediate in this reaction.
2.) what is the role of the AlCl3 in the reaction
3.) write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and include all intermediate structures
Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones
and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic
acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a
cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
HO
H
HCEN
H-3-
HO'
NaOH
HO
cyanohychin
a.
a nucleophilic substitution
b.
an electrophilic addition
C10
OH
CH-COOH
A. The reaction of an aldehyde with hydrogen cyanide is an example of
+ NaCN + H₂O
reaction.
H-
C.
an electrophilic substitution
d. a nucleophilic addition
B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.
Chapter 22 Solutions
Organic Chemistry - With Access (Custom)
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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