Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 4, Problem 81P
a. Using the wedge-and-dash notation, draw the nine stereoiomers of 1,2,3,4,5,6-hexacblorocyclohexane.
b. from the nine stereoisomers, identify one pair of enantiomers.
c. Draw the most stable conformer of the most stable stereoisomer.
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For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.
b.Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d.Which isomer, cis or trans, is more stable and why?
1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman
projection and the chair drawing. Calculate the energies of each. What ratio of the two
conformers will be present at equilibrium?
2. Draw a structure of a chiral alcohol.
For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for
substituents.
b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d. Which isomer, cis or trans, is more stable and why?
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Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Prob. 7PCh. 4.3 - Prob. 8PCh. 4.4 - Prob. 10PCh. 4.4 - Prob. 11PCh. 4.6 - Prob. 12P
Ch. 4.7 - Prob. 14PCh. 4.7 - Prob. 16PCh. 4.7 - Prob. 17PCh. 4.7 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 20PCh. 4.9 - Prob. 21PCh. 4.9 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.10 - Prob. 23PCh. 4.10 - Prob. 24PCh. 4.11 - Prob. 26PCh. 4.11 - Prob. 27PCh. 4.11 - Prob. 28PCh. 4.11 - The stereoisomer of cholesterol found in nature is...Ch. 4.11 - Prob. 30PCh. 4.12 - Prob. 31PCh. 4.12 - Draw all possible stereoisomers for each of the...Ch. 4.12 - Prob. 33PCh. 4.12 - Of all the possible cyclooctanes that have one...Ch. 4.12 - Prob. 35PCh. 4.12 - Prob. 36PCh. 4.13 - Which of the following compounds has a...Ch. 4.13 - Prob. 39PCh. 4.14 - Prob. 40PCh. 4.14 - Name the isomers you drew in Problem 52.Ch. 4.14 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.14 - Draw a perspective formula for each of the...Ch. 4.14 - Name the following:Ch. 4.14 - Prob. 45PCh. 4.14 - Prob. 48PCh. 4.14 - Prob. 50PCh. 4.15 - Limonene exists as two different stereoisomers....Ch. 4.16 - Prob. 52PCh. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Which of the following has an achiral...Ch. 4 - Prob. 63PCh. 4 - Prob. 64PCh. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Prob. 72PCh. 4 - Prob. 73PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 75PCh. 4 - Prob. 76PCh. 4 - Draw structures for the following: a....Ch. 4 - Prob. 78PCh. 4 - Prob. 79PCh. 4 - Prob. 80PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 86PCh. 4 - Is the following compound optically active?
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