Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 16, Problem 32P
Interpretation Introduction
Interpretation:
The required compounds from the given reactant are to be synthesized.
Concept introduction:
The reaction of benzene with acid chlorides or acid anhydride in the presence of a Lewis acid catalyst, such as,
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5. A solution of sucrose is fermented in a vessel until the evolution of CO2 ceases. Then, the
product solution is analyzed and found to contain, 45% ethanol; 5% acetic acid; and 15%
glycerin by weight.
If the original charge is 500 kg, evaluate;
e. The ratio of sucrose to water in the original charge (wt/wt).
f. Moles of CO2 evolved.
g. Maximum possible amount of ethanol that could be formed.
h. Conversion efficiency.
i. Per cent excess of excess reactant.
Reactions:
Inversion reaction: C12H22O11 + H2O →2C6H12O6
Fermentation reaction: C6H12O6 →→2C2H5OH + 2CO2
Formation of acetic acid and glycerin: C6H12O6 + C2H5OH + H₂O→ CH3COOH + 2C3H8O3
Show work. don't give Ai generated solution. How many carbons and hydrogens are in the structure?
13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
2°C. +2°C. cleavage
Bond A
•CH3 + 26.← Cleavage
2°C. +
Bond C
+3°C•
CH3 2C
Cleavage
E
2°C. 26.
weakest bond
Intact molecule
Strongest 3°C 20.
Gund
Largest
argest
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
C
Weakest
bond
A
Produces
Most
Bond
Strongest
Bond
Strongest Gund
produces least stable
radicals
Weakest
Stable radical
b. (4pts) Consider the relative stability of all cleavage products that form when bonds A,
B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B,
and C are all carbon radicals.
i. Which ONE cleavage product is the most stable? A condensed or bond line
representation is fine.
13°C. formed in
bound C
cleavage
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
• CH3
methyl radical
Formed in Gund A Cleavage
c.…
Chapter 16 Solutions
Organic Chemistry
Ch. 16 - PRACTICE PROBLEM 16.1 (a) Give IUPAC substitutive...Ch. 16 - Prob. 2PPCh. 16 - Prob. 3PPCh. 16 - Practice Problem 16.4
Provide the reagents and...Ch. 16 - Prob. 5PPCh. 16 - Prob. 6PPCh. 16 - Prob. 7PPCh. 16 - Prob. 8PPCh. 16 - Prob. 9PPCh. 16 - Practice Problem 16.10
Shown below is the...
Ch. 16 - Prob. 11PPCh. 16 - Practice Problem 16.12
What product would be...Ch. 16 - Prob. 13PPCh. 16 - Practice Problem 16.14
Dihydropyran reacts readily...Ch. 16 - Practice Problem 16.15 Show how you might use...Ch. 16 - Practice Problem 16.16 (a) Show how you might...Ch. 16 - Practice Problem 16.17
In addition to...Ch. 16 - Practice Problem 16.18
Triphenylphosphine can be...Ch. 16 - Prob. 19PPCh. 16 - PRACTICE PROBLEM 16.20
Give the structure of the...Ch. 16 - PRACTICE PROBLEM 16.21 What would be the major...Ch. 16 - Prob. 22PCh. 16 - 16.23 Write structural formulas for the products...Ch. 16 - Give structural formulas for the products formed...Ch. 16 - 16.25 What products would be obtained when...Ch. 16 - Predict the major organic product from each of the...Ch. 16 - 16.27 Predict the major product from each of the...Ch. 16 - 16.28 Predict the major product from each of the...Ch. 16 - Prob. 29PCh. 16 - 16.30 Write detailed mechanisms for each of the...Ch. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Show how you would convert benzaldehyde into each...Ch. 16 - 16.34 Show how ethyl phenyl ketone could be...Ch. 16 - Show how benzaldehyde could be synthesized from...Ch. 16 - Give structures for compounds AE. Cyclohexanol...Ch. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - 16.43 The structure of the sex pheromone...Ch. 16 - Provide reagents that would accomplish each of the...Ch. 16 - Write a detailed mechanism for the following...Ch. 16 - Prob. 46PCh. 16 - Dutch elm disease is caused by a fungus...Ch. 16 - Prob. 48PCh. 16 - Compounds W and X are isomers; they have the...Ch. 16 - Compounds Y and Z are isomers with the molecular...Ch. 16 - Compound A (C9H18O) forms a phenylhydrazone, but...Ch. 16 - Compound B (C8H12O2) shows a strong carbonyl...Ch. 16 - Prob. 53PCh. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - (a) What would be the frequencies of the two...Ch. 16 - Prob. 57PCh. 16 - Prob. LGP
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