Alcohol Reactions

Reducing Carbonyl to OH

Nabh4 - ketone, aldehyde

LiAlH4 - carboxylic, esters

then H30+

OH > inverted Cl

SOCl2, pyradine

1)TsCL,py 2)NaBr. or PBr3

reduction vs oxidation

reduction - carbonyl to OH, decrease O increase H

Oxidation - OH to carbonyl

make ether

OH > 1)NaH 2) alkyl halide

NaH makes alkoxide (conj base of OH, O-

charge goes to carbon arrow kicks off halide

making epoxide

mCPBA / Ch2Cl2

halohydrin Br & OH > Naoh

opening epoxide

Base/alkiline - attack less subs

Acidic- attack more substituted

stereochem inverted where nuc attacked/group adds

make aldehyde

Primary OH > PCC, DMP, Swern

CH2Cl2 solvent

1)DMSO, (COCL)2

2) Et3N

Make ketone

Secondary OH >PCC, Swern, chromic acid

make carboxylic acid

Primary OH > H2CrO4,

Na2Cr2O7, H2SO4, H2O (Chromium turns primary OH into carboxylic

Grignard reaction

Carbonyl > OH + alkyl group

1)RMgBr 2)H30+

cannot do iin acidic conditons (OH, Carboxylic

Grignard mechanism

bond on Mg attacks carbonyl pi, pi e- onto the OH

alkoxide (O-) charge goes to H bond to O of H3O+, protonating the O-

ester - 1st step same addition, alkoxide charge to O single bond to reform pi bond, arrow from its own bond onto ether kicking it off, reattack ketone base adding alkyl again, alkoxide gets protonated by h30+

grignard. on epoxide

attackes less subs and inverts attacked carbon, other stays same stereo

switch OH and X on tertiary halide

either HX or water

Naoh for primary

OH > zaitzev

conc H2SO4

OH straight to zaitzev alkene

Replace OH in primary alkyl halide

NaOCH3 - ether

NaSH - thiol

NaCO2CH3

oxidizign OH

primary - aldehyde or COOH

secondary - ketone

tertiary nr

Naming

longest chain including OH, lowest locant (OH over alkene

ether (just ether name substitients on ether side alphabetical, shorter side thoxy rest is parent chain

opening epoxide mechanism

acid - from O to H to center to protonate O, to side of epoxide up to O

basic - to side of epoxide up to O (alkoxide) O- to H bond to center to pronate