Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 29.6, Problem CQ
Interpretation Introduction
Interpretation:
The propagation step involving chain
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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
Bond A
Bond C
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
Weakest
Bond
Strongest
Bond
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.
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
c. (5pts) Use principles discussed in lecture, supported by relevant structures, to
succinctly explain the why your part b (i) radical is more stable than your part b(ii)
radical. Written explanation can be no more than one-two succinct sentence(s)!
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Statifically more chances to abstract one of these 6H
11. (10pts total) Consider the radical chlorination of 1,3-diethylcyclohexane depicted below. 4
4th total
• 6H total
래
• 4H total
21 total
ZH
2H
Statistical
H < 3° C-H weakest
-
product
abstraction here
bund
leads to thermo favored
a) (6pts) How many unique mono-chlorinated products can be formed and what are the
structures for the thermodynamically and statistically favored products?
Product
6
Number of Unique
Mono-Chlorinated Products
Thermodynamically
Favored Product
Statistically
Favored Product
b) (4pts) Draw the arrow pushing mechanism for the FIRST propagation step (p-1) for the
formation of the thermodynamically favored product. Only draw the p-1 step. You do
not need to include lone pairs of electrons. No enthalpy calculation necessary
H
H-Cl
Waterfox
10. (5pts) Provide the complete arrow pushing mechanism for the chemical transformation →
depicted below
Use proper curved arrow notation that explicitly illustrates all bonds being broken, and
all bonds formed in the transformation.
Also, be sure to include all lone pairs and formal charges on all atoms involved in the
flow of electrons.
CH3O
II
HA
H
CH3O-H
H
①
Chapter 29 Solutions
Organic Chemistry
Ch. 29.2 - Prob. 29.1PCh. 29.5 - Prob. 29.2PCh. 29.6 - Prob. AQCh. 29.6 - Prob. BQCh. 29.6 - Prob. CQCh. 29.6 - Prob. DQCh. 29.6 - Prob. EQCh. 29.6 - Prob. FQCh. 29.6 - Prob. 29.3PCh. 29.6 - Prob. 29.4P
Ch. 29 - Prob. 29.5PCh. 29 - Prob. 29.6PCh. 29 - Prob. 29.7PCh. 29 - Prob. 29.8PCh. 29 - Prob. 29.9PCh. 29 - Prob. 29.10PCh. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Prob. 29.13PCh. 29 - Prob. 29.14PCh. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 29 - Polycarbonates (Section 29.5C) are also formed by...Ch. 29 - Prob. 29.18PCh. 29 - Prob. 29.19PCh. 29 - Prob. 29.20PCh. 29 - Prob. 29.21PCh. 29 - Draw a structural formula of the polymer resulting...Ch. 29 - Prob. 29.23PCh. 29 - Prob. 29.24PCh. 29 - Prob. 29.25PCh. 29 - Select the monomer in each pair that is more...Ch. 29 - Prob. 29.27PCh. 29 - Prob. 29.28PCh. 29 - Prob. 29.29PCh. 29 - Prob. 29.30PCh. 29 - Prob. 29.31PCh. 29 - Prob. 29.32PCh. 29 - Prob. 29.33PCh. 29 - Radical polymerization of styrene gives a linear...Ch. 29 - Prob. 29.35PCh. 29 - Prob. 29.36PCh. 29 - Prob. 29.37PCh. 29 - Prob. 29.38P
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