Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 7, Problem 2CTQ
Interpretation Introduction
Interpretation: The information obtained from each part of the name of molecule in model 1 needs to be explained.
Concept Introduction:
The cis and trans isomerism concept will be applied here. Any molecule will be called cis if it follows the conditions for it that is the same groups attached either above the plane or below the plane.For trans isomer, same groups are attached where one is above the plane and other group is below the plane or vice versa.
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The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).
Draw all constitutional isomers of all-cis ethylmethylisopropylcyclohexane—that is, in which a methyl group (CH3), an ethyl group (CH2CH3), and an isopropyl group [CH(CH3)2] are all bonded to a cyclohexane ring on the same side of the ring’s plane. Which of those isomers do you think is the most stable? Explain
[Review Topics]
[References]
Calculate Strain energy for the conformer pictured below, using strain energy increments from the table.
Strain Energy for Alkanes
Interaction / Compound kJ/mol
H: H eclipsing
H: CH3 eclipsing
CH3 CH3 eclipsing
gauche butane
cyclopropane
cyclobutane
cyclopentane
cycloheptane
cyclooctane
H₂
H
(Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case
sensitive.)
CH3
CH3
H
4.0
5.8
11.0
3.8
115
110
26.0
26.2
40.5
H
kcal/mol
1.0
1.4
2.6
0.9
27.5
26.3
6.2
6.3
9.7
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Chapter 7 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 7 - Prob. 1CTQCh. 7 - Prob. 2CTQCh. 7 - Prob. 3CTQCh. 7 - Draw wedge and dash skeletal representations of...Ch. 7 - Label each ring in Figure 7.2 cis or trans.Ch. 7 - Prob. 6CTQCh. 7 - Prob. 7CTQCh. 7 - Prob. 8CTQCh. 7 - a model of cyclohexane in a chair conformation,...Ch. 7 - Prob. 10CTQ
Ch. 7 - Prob. 11CTQCh. 7 - Fill in the blanks: cis-1,3-Dimethylcyclohexane...Ch. 7 - Prob. 13CTQCh. 7 - Prob. 14CTQCh. 7 - Prob. 15CTQCh. 7 - Prob. 16CTQCh. 7 - Prob. 17CTQCh. 7 - Prob. 18CTQCh. 7 - Draw chair representations of...Ch. 7 - Which stereoisomer in the previous question is...Ch. 7 - Prob. 21CTQCh. 7 - Prob. 1ECh. 7 - Label each of the following as cis, trans or...Ch. 7 - Which pair has more in common with one another?Ch. 7 - Prob. 4ECh. 7 - Prob. 5ECh. 7 - Prob. 6ECh. 7 - Fill in the table by drawing a representation of a...Ch. 7 - Prob. 9ECh. 7 - True or False: If you perform a chair flip on...Ch. 7 - Prob. 11ECh. 7 - Prob. 12ECh. 7 - Prob. 13ECh. 7 - Prob. 14ECh. 7 - Prob. 15ECh. 7 - Draw trans-1-tert-butyl-3-methylcyclohexane in its...Ch. 7 - Build a model of methylcyclohexane, and use the...
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