Chem 212 Enolate Problem Set

ANSWERS O MeO O MeO O OMe 1) NaOMe 2) Br no asymmetric carbons O OMe

Provide the products for the following reactions. O 1) LDA
*

O

2)

Br

racemic O O O MeO Br O OMe 1) NaOMe 2) Br HO no asymmetric carbons O O O OEt racemic 1) NaOEt 2) Br
*

O 1) LDA 2)

racemic O

3) H3O+, heat O OEt racemic

O 1) Me2CuLi 2) H3O+

O 1) Et MgBr 2) H3O+ O 1) LDA MeO 2) Br 3) H3O+ O 1) LDA O 2) Br
*

O OH racemic

O OEt

O 1) NaOEt 2) Br

no asymmetric carbons

3) H3O+, heat O O O MeO O O racemic O OEt O H EtO O O OEt 1) NaOEt 2) 3) H3O+, heat O 1) NaOEt 2) Et Br 3) NaOEt 4) Br 5) H3O+, heat O 1) NaOEt 2) MeI racemic O O O NaH OTs single enantiomer O 1) NaOMe 2) Br O O no asymmetric carbons O
*

OH Br no asymmetric carbons O

O
*

racemic

O

O

O no asymmetric carbons

O racemic

O

O

1) NaOEt 2) Br

5-membered rings form faster than 7-membered ones MeO H O CO O O H O 1) KOtBu 2) MeI 3) KOtBu 4) O I H H O
*

MeO O OtBu 1) LDA 2) Br

single enantiomer

O mixture of diastereomers

CO2Me 1) 1,2-ethanediol, H+ 2) NH3, H2O, heat

HN
*

O HO2C N CHO 1) NaBH4, MeOH 2) Ac2O, pyridine

O single enantiomer

O

* 3) LiAlH4 4) excess H3O+ (2 steps in one) O 5) (conjugate addition!) mixed diastereomers 1) form ketal 2) ester to amide 3) reduce amide to primary amine 4) neutralize LiAlH4 reaction AND cleave ketal 5) amine does conjugate acid addition

N

1) reduce aldehyde (only!) to primary alcohol 2) form anhydride from alcohol which reacts with carboxylic acid to form lactone

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