experiment- Reduction of 4-tert-butylcyclohexanone question- How might 1H NMR be used to distinguish between the cis and trans alcohol products that form?

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experiment- Reduction of 4-tert-butylcyclohexanone

question- How might 1H NMR be used to distinguish between the cis and trans alcohol products that
form? 

Experiment - Reduction of t-butylcyclohexanone ធ
A
Q ↑↓
+ 100%
The first step in this reaction is the transfer of a hydride ion to the carbon of the carbonyl. The hydride
acts as a nucleophile and attacks the carbon of the carbonyl. The hydride can either come in via an
axial attack or an equatorial attack depending on steric factors and the placement of other substituents
on the ring. Below is the reaction scheme. Take note that some arrows are missing so be sure to
include those when writing the mechanism in your prelab report. Typically, the axial attack is preferred
over the equatorial attack, leading to the alcohol in the equatorial position. This type of reaction is
stereoselective since one stereoisomer is preferred over another. For the reaction in this week's
experiment, a mixture of diasteriomeric alcohols will be produced and analyzed.
1 of 4
(H3C)3C-
ملے اور میں
Figure 1
axial attack
equatorial attack
(H3C)3C-
(H3C)3C-
H
H
H
HⓇ
(H3C)3C-
(H3C)3C-
90% trans
10% cis
H
OH
OH
H
If a more sterically hindered reducing agent is used, then the opposite product ratio is observed. If they
were to make an axial attack, these hydride reagents would sterically clash with 1,3-diaxial hydrogen
atoms.
Transcribed Image Text:Experiment - Reduction of t-butylcyclohexanone ធ A Q ↑↓ + 100% The first step in this reaction is the transfer of a hydride ion to the carbon of the carbonyl. The hydride acts as a nucleophile and attacks the carbon of the carbonyl. The hydride can either come in via an axial attack or an equatorial attack depending on steric factors and the placement of other substituents on the ring. Below is the reaction scheme. Take note that some arrows are missing so be sure to include those when writing the mechanism in your prelab report. Typically, the axial attack is preferred over the equatorial attack, leading to the alcohol in the equatorial position. This type of reaction is stereoselective since one stereoisomer is preferred over another. For the reaction in this week's experiment, a mixture of diasteriomeric alcohols will be produced and analyzed. 1 of 4 (H3C)3C- ملے اور میں Figure 1 axial attack equatorial attack (H3C)3C- (H3C)3C- H H H HⓇ (H3C)3C- (H3C)3C- 90% trans 10% cis H OH OH H If a more sterically hindered reducing agent is used, then the opposite product ratio is observed. If they were to make an axial attack, these hydride reagents would sterically clash with 1,3-diaxial hydrogen atoms.
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