Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 22.2, Problem 2P
Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating
a. similarities.
b. differences.
- 1. acid-catalyzed formation of a hydrate (Section 16.9)
- 2. acid-catalyzed conversion of an
aldehyde to a hemiacetal (Section 16.9) - 3. acid-catalyzed conversion of a hemiacetal to an acetal (Section 16.9)
- 4. acid-catalyzed hydrolysis of an amide (Section 15.12)
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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box.
Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below.
Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first
stable product you expect to form in solution.
དྲ。
✗MgBr
?
O
CI
Will the first product that forms in this reaction
create a new C-C bond?
Yes
No
•
?
Will the first product that forms in this reaction
create a new CC bond?
Yes
No
×
: ☐
X
Predict the major products of this organic reaction:
OH
NaBH4
H
?
CH3OH
Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry.
Click and drag to start drawing a
structure.
☐ :
S
Predict the major products of this organic reaction:
1. LIAIHA
2. H₂O
?
Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry.
Click and drag to start drawing a
structure.
X
: ☐
Chapter 22 Solutions
Organic Chemistry (8th Edition)
Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7PCh. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9PCh. 22.7 - Prob. 10PCh. 22.7 - Prob. 12PCh. 22.7 - Prob. 13P
Ch. 22.9 - Which of the following amino acid side chains can...Ch. 22.9 - Which of the following C-terminal peptide bonds is...Ch. 22.9 - Carboxypeptidase A has esterase activity as well...Ch. 22.10 - Arginine and lysine side chains fit into trypsins...Ch. 22.10 - Explain why serine proteases do not catalyze...Ch. 22.11 - If H2 18O is used in the hydrolysis reaction...Ch. 22.11 - Draw the pH-activity profile for an enzyme that...Ch. 22.12 - The pHactivity profile for glucose-6-phosphate...Ch. 22.12 - Prob. 23PCh. 22.13 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 22.13 - What advantage does the enzyme gain by forming an...Ch. 22.13 - Prob. 26PCh. 22.13 - Prob. 27PCh. 22.13 - Aldolase shows no activity if it is incubated with...Ch. 22 - Which of the following parameters would be...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Indicate the type of catalysis that is occurring...Ch. 22 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 22 - Prob. 34PCh. 22 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 22 - there are two kinds of aldolases. Class I...Ch. 22 - Prob. 37PCh. 22 - The hydrolysis of the ester shown here is...Ch. 22 - Prob. 39PCh. 22 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 22 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 22 - Proof that an imine was formed between aldolase...Ch. 22 - Prob. 43PCh. 22 - a. Explain why the alkyl halide shown here reacts...Ch. 22 - Triosephosphate isomerase (TIM) catalyzes the...
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