Aldehydes + Ketones updated FC

what is a geminol diol

two alcholol groups

What is an imine

Double bonded N with an R group attached

Imine formation

Aldehyde/ketone + H₂NR

Cyanohydrine formation

Aldehyde/ketone + HCN

What is a cyanohydrine (and what usually happens to it)

An alchohol and CN group

usually gets reduced where the CN turns into a carboxylic acid

Wittig reaction

Double bonded PPh₃ + double bonded O

Combine the double bonds

Enamine formation

Aldehyde/ketone + NHR₂

Will have a double bond not with the N but with a C (because another H is taken)

Hydroxylamine

Aldehyde/ketone + HONH₂ = double bonded NOH replacing the double bonded O

Hydrazine

Aldehyde/ketone + H₂NNH₂ = double bonded NNH replacing the double bonded O

Wolff-kishner

Aldehyde/ketone + H₂NNH₂/heat + H₂O → double bonded O gets repalced with two H

LAH vs NaBH₄

LAH: will attack ester + Ketone

NaBH₄ only attacks ketones

Organometallics

Only attack once

Ways to make aldehydes

1. Primary alchol + PCC

2. alkene + O₃ and then a reduction (Zn/Hcl, Sn/HCl, DMS, PPh₃)

Ways to make ketones

1. Tetraconjugated alkene + O₃/H2O

2. Caroxylic acid + PCC or strong oxidized (KMnO₄)

Common ways to reduce Ketones + Aldehydes to alkanes

1. Zn(Hg), HCL + heat

2. H₂NNH₂, KOH + heat

Will not work: H₂/Pd (only if benzyllic)

reduction: gets rid of double bond O and repalces with two H

Common ways to reduce Ketones + Aldehydes to alcohols

Aldehyde + LAH or NaBH₄ → OH gets adds to where the H was

Ketone + LAH or NaBH₄ → OH gets added to where O was

Ketones + aldehydes with water

forms a geminal diol

Ketones + Aldehydes with alcohols

1 eq. will form a hemi acetal/ketal

2 eq. will form a acetal/ketal