Alcohol Synthesis

Front 1

aq KMnO4

Back 1

Alcohol from alkene;Hydroxylation;glycol;syn addition

Front 2

H2O, H2SO4

Back 2

alcohol from alkene;Markov;rearragnment possible w/ carbocation;non sterospecific
if chiral then racemic, disteromer

Front 3

1)Hg(OAc)2 H2O (any alcohol, protic nucleophile)
2)NaBH4

Back 3

Markov alcohol from alkene;no rearrangement,no carbocation;non stereospecific;Oxymec/Demerc

Front 4

1)Mg(Grinard) and dry ether
2)(product from 1) + formadalhyde

Back 4

1)Magnesium Br from Br
2)alcohol

Front 5

1)dry ether, NaBH4
2)H3O+

Back 5

less substituted alcohol from keytone

Front 6

1)KOAc, DMF
2)H30+ (or any water)

Back 6

alcohol from halogen;SN2

Front 7

NaOH, H2O

Back 7

SN2, racomerzation, alcohol from halogen

Front 8

1)dry ether
2)H3O+

Back 8

double bond alcohol from double bond

Front 9

carbonyl attached to a cyclopentane + CH3CH2CHCH3 + dry ether
______MgBr
2)H2O

Back 9

alcohol and sec-butyl attached where carbonyl was

Front 10

1)Mg(Grinard) and dry ether
2)(product from + oxyrane and dry ether
3)H2O

Back 10

1)CH2CH2OMgBr from MgBr
2)CH2CH2OH

Front 11

1)LiAlH4 or NaBH4,(C2H5)2O(dry ether) or THF
2)H3O+(or H2O or D2O)

Back 11

forms an alcohol from aldehyde(1° alc) or keytone(2° alc)

Front 12

H2, Pt or Ni

Back 12

Alcohol from aldehyde and keytones;catalytic hydrogenation;reduces all C=C bonds;Reduction of carbonyls

Front 13

1)LiAlD4, dry ether
2)H2O

Back 13

1)D on one of C=O bonds
2)H bonds w/ O to make OH

Front 14

1)LiAlH4 or NaBH4, dry ether
2)H2O (or D2O or H3O+)

Back 14

alcohol from carbonyl; only C=O bonds reduced

Front 15

Pt(catalyst)/H2, NaBH4)
LiAlH4

Back 15

2° alcohol from keytone;1° from aldehyde;CH3MgI from CH3I + Mg;MgBr from Br + Mg in THF

Front 16

1)B2H6
2)H2O,NaOH

Back 16

alcohol from alkene,contra Markov,syn