Key Principles of Organic Synthesis - Oxidation and Reduction

Practice flashcards covering the key principles of organic synthesis involving the oxidation and reduction of carbonyl compounds.

Oxidation Level

The number of bonds from a carbon atom to a more electronegative atom within a functional group.

Functional Group Interconversion (FGI)

The process of selectively increasing or decreasing the oxidation level of a compound to convert one functional group into another.

Jones Oxidation

The oxidation of primary alcohols to aldehydes and secondary alcohols to ketones using $K_2Cr_2O_7$ in $H_2SO_4$.

Pyridinium chlorochromate (PCC)

A metal-based oxidant developed to be more soluble in organic solvents than traditional chromate salts, used to oxidize alcohols.

Swern Oxidation

A mild, metal-free oxidation method using DMSO, oxalyl chloride, and $Et_3N$ to convert primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation.

$NaBH_4$ (Sodium Borohydride)

A hydride-based reducing agent used to reduce aldehydes and ketones to their respective alcohols; it is less reactive than $LiAlH_4$.

$LiAlH_4$ (Lithium Aluminium Hydride)

A powerful reducing agent that can reduce various carbonyl functionalities, including converting esters to primary alcohols and amides to amines.

DIBAL (Di-isobutylaluminium hydride)

A bulky reducing agent used for the selective reduction of esters to aldehydes at low temperatures, typically $-78\,^\circ\text{C}$.

Hemi-acetal Coordination Complex

A stable intermediate formed during DIBAL reduction at low temperatures that prevents over-reduction to an alcohol until water or acid is added.

Wolff-Kischner Reduction

A method to reduce aldehydes and ketones to alkanes using hydrazine ($NH_2NH_2$) and base ($KOH$) at high temperatures (approx. $200\,^\circ\text{C}$).

Clemmensen Reduction

A method to reduce ketones, particularly aromatic ones, to alkanes using a zinc-mercury amalgam ($Zn\text{-}Hg$) under strongly acidic conditions ($HCl_{\text{(aq)}}$).

Redox Chemistry

The study of the ability to selectively increase (oxidation) or decrease (reduction) the oxidation level of a compound.