Question

1. Draw all the products from the reaction of KCN in the presence of H2SO4 to the ketones A and B. Explain whether or not a new chiral centre is generated in this process. Me Me O A Me Me O B single enatiomer 2. Predict the structure of the major product formed by reduction of the ketone A with aluminium prop-2-oxide in propan-2-ol. Rationalise the stereochemical outcome for this reaction. O A Al(OCHMe2)3 in Me2CHOH OH B 3. Account for the difference in selectivity upon reduction of the bicyclic ketones A and B with NaBH4 in MeOH. O A NaBH4 MeOH H OH endo-C O B NaBH4 MeOH OH H exo-D 4. Reduction of the ketone A with L-Selectride™, LiBH[CH(Me)Et]3 gave a diastereoisomeric mixture (ratio 93:7) of the alcohols syn- and anti-B. Account for this observation. O A LiBH[CH(Me)Et]3 then MeOH OH syn-B + OH anti-B 93 : 7

          1. Draw all the products from the reaction of KCN in the presence of H2SO4 to the ketones A and B. Explain whether or not a new chiral centre is generated in this process.
Me Me
O
A
Me Me
O
B
single enatiomer
2. Predict the structure of the major product formed by reduction of the ketone A with aluminium prop-2-oxide in propan-2-ol. Rationalise the stereochemical outcome for this reaction.
O
A
Al(OCHMe2)3 in Me2CHOH
OH
B
3. Account for the difference in selectivity upon reduction of the bicyclic ketones A and B with NaBH4 in MeOH.
O
A
NaBH4 MeOH
H OH
endo-C
O
B
NaBH4 MeOH
OH H
exo-D
4. Reduction of the ketone A with L-Selectride™, LiBH[CH(Me)Et]3 gave a diastereoisomeric mixture (ratio 93:7) of the alcohols syn- and anti-B. Account for this observation.
O
A
LiBH[CH(Me)Et]3 then MeOH
OH
syn-B
+
OH
anti-B
93 : 7

1. Draw all the products from the reaction of KCN in the presence of H2SO4 to the ketones A and B. Explain whether or not a new chiral centre is generated in this process.
Me Me
O
A
Me Me
O
B
single enatiomer
2. Predict the structure of the major product formed by reduction of the ketone A with aluminium prop-2-oxide in propan-2-ol. Rationalise the stereochemical outcome for this reaction.
O
A
Al(OCHMe2)3 in Me2CHOH
OH
B
3. Account for the difference in selectivity upon reduction of the bicyclic ketones A and B with NaBH4 in MeOH.
O
A
NaBH4 MeOH
H OH
endo-C
O
B
NaBH4 MeOH
OH H
exo-D
4. Reduction of the ketone A with L-Selectride™, LiBH[CH(Me)Et]3 gave a diastereoisomeric mixture (ratio 93:7) of the alcohols syn- and anti-B. Account for this observation.
O
A
LiBH[CH(Me)Et]3 then MeOH
OH
syn-B
+
OH
anti-B
93 : 7

Added by Stephanie M.

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