Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 23.2, Problem 5P
Instead of adding to the 4a position and protonating N-5, the thiolate ion could have added to the 10a position and protonated N-l. (The numbering system is on page 1071.) Why is addition to the 4a position favored? (Hint: Which nitrogen is a stronger base?)
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Predict the position of the equilibrium for the reaction and provide a brief explanation.
(The acidic protons are shown in red.)
to
to
OH
CH3-
CH3-OH
A
D
Forward direction is favored because C is not well solvated, making Ca stronger base than B.
Forward direction is favored because C is not well solvated, making Ca weaker base than B.
Reverse direction is favored because C is not well solvated, making Ca weaker base than B.
Reverse direction is favored because C is not well solvated, making Ca stronger base than B.
Explain why the C – Ha bond is much more acidic than the C – Hb bond in pentan-2-one.
ONANO
(a) Circle the two compounds that are not carboxylic acid derivatives. Circle only two.
CONHCH3
CN
=NOH
NH
COCI
(b) Circle the two compounds that can be hydrolyzed to a ketone in aqueous acid. Circle only two.
N-PH
(c) Circle the two compounds that can be converted to an aldehyde by reduction using DIBAL (also known as
DIBAL-H). Circle only two.
.CHO
он
CN
(d) Circle the two most reactive compounds with water. Circle only two
DEt
OMe
NH2
CH;CH,CN
(e) Circle the strongest acid. [2 marks]
CO.Et
CO-H
NO2
CHO
(1) Circle ethyl benzoate and maleic anhydride.
COCH,CH,
.Co.CH,CH3
(g) Circle the two compounds that can be reduced to an amine using NaBH4. Circle only two.
'NH2
CN
NH
Chapter 23 Solutions
Organic Chemistry (8th Edition)
Ch. 23.1 - Prob. 2PCh. 23.1 - Prob. 3PCh. 23.2 - How many conjugated double bonds are there in a....Ch. 23.2 - Instead of adding to the 4a position and...Ch. 23.2 - Prob. 7PCh. 23.3 - Prob. 8PCh. 23.3 - Acetolactate synthase is another TPP-requiring...Ch. 23.3 - Acetolactate synthase transfers the acyl group of...Ch. 23.3 - Prob. 12PCh. 23.5 - Which compound is more easily decarboxylated?
Ch. 23.5 - Prob. 14PCh. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - The enzyme that catalyzes the C C bond cleavage...Ch. 23.5 - Propose a mechanism for the ,-elimination reaction...Ch. 23.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 23.6 - Prob. 20PCh. 23.7 - How do the structure of tetrahydrofolate and...Ch. 23.7 - What is the source of the methyl group in...Ch. 23.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 23 - How does the metal ion in carboxypeptidase A...Ch. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - For each of the following reactions, name both the...Ch. 23 - Prob. 27PCh. 23 - When transaminated, the three branched-chain amino...Ch. 23 - What acyl groups have we seen transferred by...Ch. 23 - Propose a mechanism for the following reaction:Ch. 23 - Draw the products of the following reaction, where...Ch. 23 - When UMP is dissolved in T2O, exchange of T for H...Ch. 23 - Dehydratase is a PLP-requiring enzyme that...Ch. 23 - In addition to the reaction mentioned in Section...Ch. 23 - PLP can catalyze both ,-elimination reactions...Ch. 23 - The glycine cleavage system is a group of four...Ch. 23 - Prob. 37PCh. 23 - FADH2 reduces , -unsaturated thioesters to...
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