Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
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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7. For compound A in acid, it is the hydroxyl that is protonated
to a greater extent than the carbonyl oxygen. However, for
compound B in acid, it is the carbonyl oxygen that is
protonated to a greater extent than the hydroxyl oxygen.
Explain this difference.
H2SO4
ОН
ОН2
ОН
H2SO4
ОН
ОН
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.
Draw the conjugate acid that is formed as a product in this reaction.
Chapter 23 Solutions
Organic Chemistry, Books a la Carte Edition (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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