3. Please convert the wedge-dashed structure to a chair conformation, flip it, and determine which chair is most stable. Please draw the chairs and substituents with the correct angles. Label each group axial (a) or equatorial (e). A-Values Measure the size of organic groups A-Value Group -H -F -CI -Br -1 -CN -OH -SH -NH₂ -NO₂ b. a. >< ts) CO₂H CN 0.00 (hydrogen) 0.25 (fluoro) 0.5 (chloro) 0.6 (bromo) 0.61 (iodo) 0.2 (nitrile or cyano) 1.0 (alcohol) 1.21 (thiol) 1.5 (amine) 1.1 (nitro) Group -CH3 -CH₂CH3 -CH(CH3)2 -C(CH3)3 -CF3 -C6Hs -C6H11 -OCH3 -COH -CO₂ A-Value 1.74 (methyl) 1.79 (ethyl) 2.21 (isopropyl) 4.9 (tert-butyl) 2.5 (trifluoromethyl) 2.8 (phenyl) 2.2 (n-hexyl) 0.75 (methyl ether) 1.4 (carboxylic acid) 2.0 (carboxylate anion)
3. Please convert the wedge-dashed structure to a chair conformation, flip it, and determine which chair is most stable. Please draw the chairs and substituents with the correct angles. Label each group axial (a) or equatorial (e). A-Values Measure the size of organic groups A-Value Group -H -F -CI -Br -1 -CN -OH -SH -NH₂ -NO₂ b. a. >< ts) CO₂H CN 0.00 (hydrogen) 0.25 (fluoro) 0.5 (chloro) 0.6 (bromo) 0.61 (iodo) 0.2 (nitrile or cyano) 1.0 (alcohol) 1.21 (thiol) 1.5 (amine) 1.1 (nitro) Group -CH3 -CH₂CH3 -CH(CH3)2 -C(CH3)3 -CF3 -C6Hs -C6H11 -OCH3 -COH -CO₂ A-Value 1.74 (methyl) 1.79 (ethyl) 2.21 (isopropyl) 4.9 (tert-butyl) 2.5 (trifluoromethyl) 2.8 (phenyl) 2.2 (n-hexyl) 0.75 (methyl ether) 1.4 (carboxylic acid) 2.0 (carboxylate anion)
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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
Transcribed Image Text:3. Please convert the wedge-dashed structure to a chair conformation, flip it, and determine
which chair is most stable. Please draw the chairs and substituents with the correct angles. Label
each group axial (a) or equatorial (e).
Group
-H
-F
-CI
-Br
-I
-CN
-OH
-SH
-NH₂
-NO₂
b.
a.
ts)
CO₂H
CN
A-Values Measure the size of organic groups
A-Value
0.00 (hydrogen)
0.25 (fluoro)
0.5 (chloro)
0.6 (bromo)
0.61 (iodo)
0.2 (nitrile or cyano)
1.0 (alcohol)
1.21 (thiol)
1.5 (amine)
1.1 (nitro)
Group
-CH3
-CH₂CH3
-CH(CH3)2
-C(CH3)3
-CF3
-C6Hs
-C6H11
-OCH3
COH
-CO₂
A-Value
1.74 (methyl)
1.79 (ethyl)
2.21 (isopropyl)
4.9 (tert-butyl)
2.5 (trifluoromethyl)
2.8 (phenyl)
2.2 (n-hexyl)
0.75 (methyl ether)
1.4 (carboxylic acid)
2.0 (carboxylate anion)
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