2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: 1) NaCN CN 2) H* OH 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol a. Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?

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2. Our knowledge of chair conformations allows us to use them to determine a great deal about
a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single
conformation can help us learn about the spatial requirements and energetics of a reaction.
Consider the following two reaction products:
a.
NO NID
ALOH
1) NaCN
2) H+
1) NaBH4
2) H3O+
OH
Group
-H
-CN
-OH
A Value (kcal/mol)
Defined as 0
0.2 kcal/mol
1.0 kcal/mol
Draw the most stable chair conformation for each of the two products.
b. Based on the A values in the table above, do the two products have the most stable
conformation at the new stereocenter?
Transcribed Image Text:2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: a. NO NID ALOH 1) NaCN 2) H+ 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?
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