CHEM1AA3 Organic Functional Groups + Synthesis

ALKANE

Reduction of alkenes and alkynes using Pd/C/Pt + H2, SYN addition

Halogenation of alkenes with 2 halogens (intermediate: carbocation, X), breaking the alkene double bond.

ALKENE

Reduction of alkynes using Lindlar's catalyst + H2 (poisoned).

ALKYNE

Triple-bonded carbons.

ALCOHOL

Hydration of alkyl halides using H2O/NaOH (dil, cold)

Primary alcohol

OH attached to a C with no other carbons

Hydration of alkenes using dilute acid (H3O+) and water (initial: alkene and H3O+. intermediate: carbocation and H2O)

Reduction of aldehydes using NaBH4 (hydride source) + H3O+ (proton source)

HCHO (formaldehyde) using RMgX (Grignard reagent) + H3O+.

Secondary alcohol

OH attached to a C with 2 other Cs

Reduction of ketones using NaBH4 (hydride source) + H3O+ (proton source)

Aldehydes using Grignard reagent + H3O+.

Tertiary alcohol

OH attached to a C with 3 other Cs

Ketones using Grignard reagent + H3O+

Tertiary alkyl halide using ROH + alkyl leaving group.

GRIGNARD REAGENTS

MgX (halogen) attached to a carbon chain

Substitution of alkyl halides using Mg + Et2O (solvent).

ALDEHYDES

Oxidation of a primary alcohol using PCC + CH2Cl2 (solvent).

KETONES

Oxidation of a secondary alcohol using [O] (typically Mn or Cr)/PCC + CH2CL2.

CARBOXYLIC ACIDS

Oxidation of aldehydes/primary alcohols

Grignard reagents using CO2 + H3O+

Esters using H2O + H3O+ + heat.

ESTERS

Carboxylate anions undergoing substitution for a carbon chain on the negative O

Carboxylic acid and alcohol using H3O+ + heat, equilibrium controlled by water product

ETHER

Tertiary alkyl halide using alcohol and halogen leaving group (SN1).

Amine

Suffix 'amine'; Primary (NH2), secondary (NH), or tertiary (N) on a carbon chain.

Amide

Suffix name 'amide'; Double-bonded O and primary/secondary/tertiary amine on the same carbon.

Thiol

SH on a carbon chain.

Carboxylic acid anhydride

Double O - single O - double O within a carbon chain.

Arene

A benzene ring.

Aryl halide

A halogen on an arene.

Phenol

An OH on an arene.

F, Cl, Br, I, OH

F: fluoro; Cl: chloro; Br: bromo; I: iodo; OH: hydroxyl

PRIORITY OF GROUPS

1. Carboxylic acid/ester

2. Aldehyde/ketone

3. Alcohol

4. Alkene/alkane.

3 carbon chain with a methyl branch

isopropyl

C-O branch

methoxy

C-C-O

ethoxy

Benzene branch

phenyl

Benzene + a carbon branch

benzyl