Carbonyl Chemistry Reagents

NaAlH₄

reduces ketones, aldehydes, all carboxylic acid derivates

NaBH₄

reduces ketones, aldehydes, carboxylic acid derivatives (excluding malonic esters, esters, and amides)

1. O₃

2. Zn/H₃O⁺

replaces R=CH2 with with aldehyde or ketone depending on R group

(R)₂CuLi

adds to carbonyl one time, rather than until completion (due to non-reactive nature) (note: do not react with esters or carboxylic acids—carboxylic acids should be converted with SOCl₂ first)

H₂CrO₄

primary alcohol → carboxylic acid

secondary → ketone

aldehyde → carboxylic acid

PCC

primary → aldehyde

secondary → ketone

HS—(—)_x—SH, Raney Ni

ketone → alkane

SOCl₂

carboxylic acid → acyl chloride

amide → nitrile

Zn(Hg), HCl

ketone → alkane

R—MgBr, CO2

carboxylic acid

Strong Base (ex. NaOH), X₂

alpha halogenation to completion, can create good leaving groups like R—Br₃ which can be used to convert ketones into carboxylic acid (only way for this course to turn ketones into carboxylic acids)

H₂N—NH₂, KOH

reduces ketones and aldehydes into alkane, (can use blocker groups such as HO—(—)_x—OH to block the more reactive aldehydes

KMnO₄

for aromatics the reactions are as follows

Ar-Me → Ar-COH₂

Ar-R → Ar-COH₂

Ar-tBu → no rxn

Aldehyde → Carboxylic acid

^-C≡N, HC≡N

adlehyde → alcohol + cyanide group

R-C≡N, H₃O+

Ar—R—C≡N → Ar—R—COH₂

NH₂OH

replaces C=O with C=N—OH

PBr₃

replaces alcohol with Br