INTRO.TO GENERAL,ORGAN...-OWLV2 ACCESS
12th Edition
ISBN: 9781337915977
Author: Bettelheim
Publisher: CENGAGE L
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Chapter 16, Problem 52P
17-60 1-Propanol can be prepared by the reduction of an
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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 16 Solutions
INTRO.TO GENERAL,ORGAN...-OWLV2 ACCESS
Ch. 16.2 - Problem 17-1 Wrtie the IUPAC name for each...Ch. 16.2 - Prob. 16.2QCCh. 16.2 - Prob. 16.3QCCh. 16.4 - Prob. 16.4QCCh. 16.4 - Prob. 16.5QCCh. 16.4 - Problem 17-6 Show the reaction of benzaldehyde...Ch. 16.4 - Problem 17-7 Identify all hemiacetals and acetals...Ch. 16.5 - Prob. 16.8QCCh. 16 - 17-9 Answer true or false. (a) The one aldehyde...Ch. 16 - Prob. 2P
Ch. 16 - 17-11 What is the difference in structure between...Ch. 16 - 17-12 Is it possible for the carbon atom of a...Ch. 16 - 17-13 Which compounds contain carbonyl groups?Ch. 16 - 17-14 Following are structural formulas for two...Ch. 16 - 17-15 Draw structural formulas for the four...Ch. 16 - Prob. 8PCh. 16 - Prob. 9PCh. 16 - 17-18 Draw structural formulas for these ketones....Ch. 16 - 17-19 Write the JUPAC names for these compounds.Ch. 16 - Prob. 12PCh. 16 - 17-2 1 Explain why each name is incorrect. Write...Ch. 16 - Prob. 14PCh. 16 - Prob. 15PCh. 16 - 17-24 In each pair of compounds, select the one...Ch. 16 - Prob. 17PCh. 16 - 17-26 Account for the fact that acetone has a...Ch. 16 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 16 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 16 - 17-29 Why can’t two molecules of acetone form a...Ch. 16 - 17-30 Answer true or false. (a) The reduction of...Ch. 16 - 17-3 1 Draw a structural formula for the principal...Ch. 16 - Prob. 24PCh. 16 - 17-33 What simple chemical test could you use to...Ch. 16 - 17-34 Explain why liquid aldehydes are often...Ch. 16 - 17-35 Suppose that you take a bottle of...Ch. 16 - 17-36 Explain why the reduction of an aldehyde...Ch. 16 - Prob. 29PCh. 16 - Prob. 30PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - 17-47 What is the characteristic structural...Ch. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - Prob. 43PCh. 16 - Prob. 44PCh. 16 - Prob. 45PCh. 16 - 17-54 Following is the structure of...Ch. 16 - Prob. 47PCh. 16 - Prob. 48PCh. 16 - Prob. 49PCh. 16 - Prob. 50PCh. 16 - Prob. 51PCh. 16 - 17-60 1-Propanol can be prepared by the reduction...Ch. 16 - Prob. 53PCh. 16 - 17-62 Show how to bring about these conversions....Ch. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - Prob. 57PCh. 16 - Prob. 58PCh. 16 - 17-67 Draw structural formulas for these...Ch. 16 - Prob. 60PCh. 16 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 16 - 17-70 What simple chemical test could you use to...Ch. 16 - Prob. 63PCh. 16 - Prob. 64PCh. 16 - Prob. 65PCh. 16 - 17-72 The following molecule is an enediol; each...Ch. 16 - 17-73 Alcohols can be prepared by the...Ch. 16 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 16 - Prob. 69PCh. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - 17-78 Complete the following equation for these...Ch. 16 - 17-79 Write an equation for each conversion. (a)...Ch. 16 - Prob. 74P
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