Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 6, Problem 53P
cis-4-Bromocyclohexanol
Compound C has infrared absorption in the 1620–1680-cm−1 and in the 3590–3650-cm−1regions. Draw and label the (R) and (S) enantiomers of product C.
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Draw a structural formula for the substitution product of the reaction shown below.
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• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• If more than one stereoisomer of product is formed, draw both.
Separate multiple products using the + sign from the drop-down menu.
• Products that are initially formed as ions should be drawn in their neutral forms.
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Compounds 1 and 2 were prepared, and the difference in their heats of combustion was found to be 17.2 kJ/mol (J. Am. Chem. Soc.
1961, 83, 606-614):
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Shown below are the lowest-energy conformations of compounds 1 and 2. Identify which drawing matches which compound, and
identify which compound has the larger heat of combustion.
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H
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2
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4
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The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the less stable compound.
O The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the less stable compound.
The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the more stable compound.
The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the more stable compound.
For the substituted cyclohexane compound shown, identify the atoms that are trans to the bromo substituent.
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Identify the atoms that are trans to the bromine.
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Chapter 6 Solutions
Organic Chemistry
Ch. 6 - Prob. 1PPCh. 6 - Prob. 2PPCh. 6 - Prob. 3PPCh. 6 - Prob. 4PPCh. 6 - Prob. 5PPCh. 6 - PRACTICE PROBLEM 6.6
reactions that involve...Ch. 6 - PRACTICE PROBLEM 6.7 Rank the following...Ch. 6 - Prob. 8PPCh. 6 - Prob. 9PPCh. 6 - Prob. 10PP
Ch. 6 - Prob. 11PPCh. 6 - Prob. 12PPCh. 6 - Prob. 13PPCh. 6 - Prob. 14PPCh. 6 - Prob. 15PPCh. 6 - Prob. 16PPCh. 6 - Prob. 17PPCh. 6 - Prob. 18PPCh. 6 - Prob. 19PPCh. 6 - Prob. 20PCh. 6 - Prob. 21PCh. 6 - Which SN1 reaction of each pair would you expect...Ch. 6 - Prob. 23PCh. 6 - Prob. 24PCh. 6 - Listed below are several hypothetical nucleophilic...Ch. 6 - Prob. 28PCh. 6 - Write conformational structures for the...Ch. 6 - 6.28 Consider the reaction of with .
(a) Would...Ch. 6 - Prob. 33PCh. 6 - Prob. 34PCh. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - 1-Bromobicyclo[2, 2,1] heptane is extremely...Ch. 6 - When ethyl bromide reacts with potassium cyanide...Ch. 6 - Prob. 41PCh. 6 - Prob. 42PCh. 6 - When the alkyl bromides (listed here) were...Ch. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - Prob. 47PCh. 6 - 6.42 The reaction of chloroethane with water in...Ch. 6 - Prob. 49PCh. 6 - Prob. 50PCh. 6 - Prob. 51PCh. 6 - Prob. 52PCh. 6 - 1-Bromo[2.2.1] bicycloheptane is unreactive toward...Ch. 6 - Open the computer molecular model tided...Ch. 6 - Prob. 56PCh. 6 - Consider the solvolysis reaction of (1S,...Ch. 6 - 2. Consider the following sequence of reactions,...Ch. 6 - Prob. 26PCh. 6 - Your task is to prepare isopropyl methyl ether by...Ch. 6 - Prob. 29PCh. 6 - 6.53 cis-4-Bromocyclohexanol racemic C6H10O...Ch. 6 - Prob. 31PCh. 6 - Explain the following observations: When...Ch. 6 - Prob. 38PCh. 6 - Prob. 1QCh. 6 - Prob. 2QCh. 6 - 6.3 A kinetic study yielded the following reaction...Ch. 6 - Prob. 4QCh. 6 - 6.5 Supply the missing reactants, reagents,...Ch. 6 - Which SN2 reaction will occur most rapidly....Ch. 6 - 6.7 Provide three-dimensional structures for the...
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- Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardGive the IUPAC name for each compound. Part 1 of 2 Part 2 of 2 ྾ 6 ད, CH; | CH, | CH; H,C=Ç=C=C─Ç—CH, CH; 6 كا gl。 18 Ararrow_forward
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