Organic Reactions Summary

Alkanes
1. 2. 3. Combustion: Cracking: Halogenation: alkane + O2 → CO2 + H2O
heat, no O2

alkane

alkane + alkene
uv light

halogen + alkane

→ haloalkane

Alkenes
1. Oxidation reactions a) Combustion: b) moderate oxidation: 2. a) b) c) d) alkene + O2 → CO2 + H2O alkene + cold dilute KMnO4 → diol + 2 MnO2 + 2 KOH + + + + H2 → alkane X2 → dihaloalkane H2O → alcohol HX → haloalkane
Pt

Electrophilic Addition reactions Hydrogenation: alkene Halogenation: alkene Hydration: alkene with HX: alkene

Note: For the final two addition reactions, use Markovnikov's Rule – add the hydrogen to the carbon with the most hydrogens. If they have the same number of hydrogen atoms, you will have two possible products.
∆ ,P

3.

Addition Polymerization

alkene

polymer (long chain alkane)

Alkynes
1. 2. 3. Combustion: Addition reactions: Acid alkyne + O2 → CO2 + H2O see alkenes – use Markovnikov where applicable R-C CH → R-C C- + H+

Haloalkanes
1. 2. 3. 4. Nucleophilic Substitution (SN2)(1° RX, non-polar solvent, strong Nu) Nucleophilic Substitution (SN1)(3° RX, polar solvent, weak Nu) Elimination (E2)(3° RX, strong Nu) Unimolecular Elimination (E1) (3° RX, polar solvent, weak Nu) RX RX RX RX + + + + NuNuNuNu→ → → → R-Nu + XR-Nu + Xalkene + NuH + Xalkene + NuH + X-

Aromatics
1. a) Electrophilic Substitution FeX3 or AlX3 Halogenation: Benzene + X2 → halobenzene + HX Note: Alkyl side chains will readily undergo free radical halogenation without any addition to the ring. H+ b) Nitration Benzene + HNO3 → nitrobenzene + H2O c) Friedel-Crafts Alkylation FeX3 or AlX3 Benzene + RX → Benzene + RX FeX3 or AlX3 →
CH HC CH CH C CH
O C R

R

+ HCl + HCl

d) Friedel-Crafts Acylation

CH HC CH

CH C CH

ortho, para directors meta directors

activating (more reactive) - R (least) , - OR, - OH, - NR2 (greatest) none
∆ , P, Pt

deactivating (less reactive) -X -NO2, -CO2CH3

2. Hydrogenation

aromatic + H2

Alcohols
1. Oxidation a) combustion: b) mild oxidation 1° ROH (K2Cr2O7) c) moderate oxidation 1° ROH (KMnO4) d) 2° ROH (KMnO4) 2. Acid –Base a) dehydration b) condensation / elimination

→ cycloalkane

alcohol → aldehyde alcohol → carboxylic acid alcohol → ketone

H+ alcohol → alkene + H2O 2 alcohols (or 1 in excess) → ether + H2O
H2SO4

alcohol + carboxylic acid c) halogenation 3. Condensation Polymer

→ ester + H2O

HX + alcohol → haloalkane + H2O diol + dicarboxylic acid → polyester + H2O ∆ ether + HX → haloalkane + H2O ether + O2 → peroxide

Ethers
1. Halogenation 2. Peroxide

Aldehydes and Ketones
1. Hydrogenation aldehydes + H2 → 1° ROH ketones + H2 → 2° ROH aldehyde + KMnO4 → carboxylic acid
O R C R OH

2. 3.

Oxidation Nucleophilic Addition

+

N

C

-

H R N

+

OH R C C HO R O
O O N
+ -

R C C

4.

Nucleophilic Addition-Elimination
O R O C R H N

O
+

-

C N H C CH

CH C CH N
+

O

+

R C N N H C R

C

CH C N
+

O

N H

O

-

CH

CH

O

-

Carboxylic Acids
1. Acid 2. Elimination 3. Reduction carboxylic acid → carboxlyate anion + H+
H2SO4

alcohol + carboxylic acid will not reduce with H2 and Pt

ester + H2O

Esters
1. Hydrolysis

H2SO4

ester + H2O → carboxylic acid + alcohol ester + OH- → carboxylate anion + alcohol

Grignard Reagents
RX + Mg → RMgX (X does not include F) 1. 2. 3. RMgX + H2O → RH + Mg(OH)X (acid –base reaction) RMgX + CO2 → RCOOMgX → RCOOH RMgX + R’CHO → 2° ROH
O R1 C R2 R1 R1 O Mg X R2 C R3 O H

+

R3

Mg X

R2

C R3

4.

RMgX + R2CO → 3° ROH

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