Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Question
Chapter 12, Problem 33P
Interpretation Introduction
(a)
Interpretation: The number of rings and number of pi bonds in A is to be determined. And one possible structure is to be drawn.
Concept introduction: Degree of unsaturation is used to determine the total number of rings and pi bonds present in compound by just looking at the molecular formula. It does not specify the total number of rings and total number of pi bonds individually.
Interpretation Introduction
(b)
Interpretation: The number of rings and number of pi bonds in B is to be determined. And one possible structure is to be drawn.
Concept introduction: Degree of unsaturation is used to determine the total number of rings and pi bonds present in compound by just looking at the molecular formula. It does not specify the total number of rings and total number of pi bonds individually.
Interpretation Introduction
(c)
Interpretation: The number of rings and number of pi bonds in B is to be determined. And one possible structure is to be drawn.
Concept introduction: Degree of unsaturation is used to determine the total number of rings and pi bonds present in compound by just looking at the molecular formula. It does not specify the total number of rings and total number of pi bonds individually.
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7. The antioxidant BHA and BHT are commonly used as food preservatives. Dhow
how BHA and BHT can be made from phenol and hydroquinone.
OH
OH
C(CH3)3
(H3C),C,
C(CH3)3
ÓCH3
ČH3
ВНА
BHT
Classify the carbocations as 1º, 2º, or 3º, and rank the carbocations in each group in order of increasing stability.
Q8 Conformational Analysis of Cycloalkanes
In this question you will look at the conformations of the following molecule:
CH3
C
В F
CH3
D
-E
A
H3C
F
I
II
Energy Costs for Interactions in Alkane Conformers:
Computed Energy Cost (kJ/mol)*
3.8
Interaction
H+H eclipsed
H+CH3 eclipsed
CH3+CH3 eclipsed
CH3+CH3 gauche
H»CH(CH3)2 gauche
H CH(CH:)2 eclipsed
CH3+CH(CH3)2 gauche
CH3+CH(CH3)2 eclipsed
HeC(CH:)3 eclipsed
CH3+C(CH3)3 gauche
CH3+C(CH:)3 eclipsed
H+I eclipsed
I+CH3 gauche
I+CH3 eclipsed
"Values computed with Gaussian09 using B3LYP/6-31G(d) for structure optimization and
B3LYP/6-311+G(2df,3p) for the conformation energy. The calculations were performed in
the gas phase (no solvent).
*This result for t-butyl is a bit peculiar given that the value is less than that for isopropyl,
but there is an explanation that I can tell you about in office hours!
4.8
12.6
3.7
(0.0)
3.1
3.6
17.3
2.8
13.6
18.7
6.7
1.2
15.5
Steric Strain in Monosubstituted Cyclohexanes:
1,3-Diaxial strain
Y
(kJ/mol)…
Chapter 12 Solutions
Organic Chemistry (6th Edition)
Ch. 12.1 - Prob. 1PCh. 12.3 - Problem 12.2 What alkane is formed when each...Ch. 12.3 - Prob. 3PCh. 12.3 - Prob. 4PCh. 12.3 - Prob. 5PCh. 12.3 - Prob. 6PCh. 12.3 - Compound Molecular formula before...Ch. 12.4 - Problem 12.8 Draw the products formed when...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12.5 - Prob. 12PCh. 12.5 - Prob. 13PCh. 12.6 - Problem 12.14 Draw the products of each...Ch. 12.8 - Prob. 15PCh. 12.8 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12.9 - Prob. 17PCh. 12.9 - Problem 12.18 Draw the products formed when both...Ch. 12.10 - Problem 12.19 Draw the products formed when each...Ch. 12.10 - Prob. 20PCh. 12.10 - Prob. 21PCh. 12.11 - Problem 12.22 Draw the products formed when each...Ch. 12.11 - Prob. 23PCh. 12.12 - Problem 12.24 Draw the organic products in each of...Ch. 12.13 - Prob. 25PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 58PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 61P
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