18.3: Review of Ketone and Aldehyde Synthesis

So far this text has discussed aldehyde and ketone synthesis from the ozolysis of alkenes, hydration of alkynes, oxidation of alcohols, and Friedel-Crafts acylation of benzene rings.

Alkenes can be cleaved using ozone (O₃) to form aldehydes and/or ketones

Hydration of an alkyne to form aldehydes

Anti-Markovnikov addition of a hydroxyl group to an alkyne forms an aldehyde. The addition of a hydroxyl group to an alkyne causes tautomerization which subsequently forms a carbonyl.

Hydration of an alkyne to form ketones

The addition of a hydroxyl group to an alkyne causes tautomerization which subsequently forms a carbonyl. Markovnikov addition of a hydroxyl group to an alkyne forms a ketone.

Oxidation of 1^o alcohols with PCC to form aldehydes

Oxidation of 2^o alcohols to form ketones

Typically uses Jones reagent (CrO₃ in H₂SO₄) but many other reagents can be used

Friedel-Crafts acylation to form a ketone

Exercise

2. Specify the reagents to complete the reaction map below.

Answer

2.

Contributors and Attributions

• Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University)

• Prof. Steven Farmer (Sonoma State University)