OCHEM 2 REACTIONS

Alcohol

NaBH4/MeOH + (Aldehyde or Ketone)

Alcohol (Complete reduction)

LiAlH4/H2O + (Aldehyde or Ketone)

Alcohol

H2/ Pd/c + (Aldehyde or Ketone)

Oposite chiral alcohol

S-CBS or R-CBS + Carbonyl

Chiral Alcohol (S?)

NADH + Carbonyl

Stops at Aldehyde

LiALH(otBu)3 + Resonant Carbonyl

Stops at Aldehyde

DIBAl-H + Resonant carbonyl

Amine

LiAlH4/ H2O + Amide

Carboxylic acid

K2Cr2O7/ H2SO4 + terminal Alcohol

Aldehyde

PCC + Terminal Alcohol

Ketone

PCC + Secondary Alcohol

Carboxylic acid

Ag2O/ NH4OH + Aldehyde

Resonant carbonyl

NaBH4/ MeOH is a weaker reagent and will not react with

H and MgBr switch

R-MgBr + Terminal alcohol

H and Li Switch

R2-NH + R-Li

Carboxylic acid and amide

R-MgBr is a weaker reagent and will not react with

TBDMS-Cl

Alcohol to ether (Holding group)

TBAF

Removes TBDMS

Alcohol +1R group

R-CuLi +Carboxylic acid derivative

Li and MgBr

adds to carbonyl first

CuLi

adds to beta carbon first

R and O switch

Ph3P-R + Carbonyl

Remove alcohol add alkene

H2SO4/H2O + Alcohol

N-R Replaces O

R-NH2 + Carbonyl

2 OH

H2O + Ketone

2 OR

ROH + Ketone

Alcohol

What does NaOH first attack?