Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 8, Problem 41P
Interpretation Introduction
Interpretation:
The reason why the double bond of tetrachloroethene is undetectable in the bromine test for unsaturation is to be explained.
Concept Introduction:
Bromination leads to the addition reaction of
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b) i) Draw the different structural isomers of the 6-membered ring compound
[GAAIBNPAS]H6 in which there are alternating Group 13 and 15 elements.
ii) The isomers containing both B-N and AI-N bonding are the most stable.
Explain why this is the case.
ii) How would you expect the structure and reactivity of the heterocycles
[GAAIBNPAS]H6 to compare with borazine?
iv) While borazine exists as a planar ring compound, the [GAAIBNPAS]H6 ring
compounds dimerize. Explain these observations.
H
-ЕН
-E
H-E
НЕ
ЕН
E
НЕ-
ЕН
H
`E
H.
H
É-H
НЕ
E = Heteroatom
エー山、
w-I
Assuming that benzaldehyde is the limiting
reagent for the synthesis of stilbene, that
stilbene is the limiting reagent for the synthesis
of stilbene dibromide, and that stilbene
dibromide is the limiting reagent for the
synthesis of diphenylacetylene; what is the
overall % yield of diphenylacetylene from
benzaldehyde given the percentage yield of
each step of the reaction sequence as follows?
Give only two significant digits. If the answer is
a whole number with two digits, do not include
the decimal.
benza
Idehy
de
Notes:
66%
stil
be
ne
23%
stilbene
dibromi
de
66%
dipheny
lacetyle
ne
Assuming that benzaldehyde is the limiting reagent for the synthesis of stilbene, that stilbene is the limiting reagent for the synthesis of stilbene dibromide, and that stilbene dibromide
is the limiting reagent for the synthesis of diphenylacetylene; what is the overall % yield of diphenylacetylene from benzaldehyde given the percentage yield of each step of the
reaction sequence as follows? Give only two significant digits. If the answer is a whole number with two digits, do not include the decimal.
52%
87%
benzaldehyde → stilbene → stilbene dibromide
41%
Answer:
diphenylacetylene
Notes:
For our multi-step synthesis we cannot just calculate the yield based on starting amount of benzaldehyde and final amount of diphenylacetylene because your group may have been
supplemented with commercial material at one or more steps.
In truth most chemist use an excess of the least expensive reagent to increase their yield. So in our case benzyltriphenylphosphonium chloride should probably be our…
Chapter 8 Solutions
Organic Chemistry
Ch. 8 - Prob. 1PPCh. 8 - Prob. 2PPCh. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - Prob. 5PPCh. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - Prob. 10PP
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 46PCh. 8 - 8.47. Farnesene (below) is a compound found in the...Ch. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 49PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - 8.59. For each of the following questions, please...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGP
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