Summary of Organic Reactions

Hydrocarbons A. Alkanes (generally unreactive) 1. free radical substitution (not selective!) C2H6 + Cl2 C2H5Cl + HCl

2. dehydrogenation (reverse reaction is more common!) C2H6 H2C=CH2 + H2

B.

Alkenes addition to double bond

R C H C H H + H X R H X C C H H H

HX where X = Cl, Br, I, or OH (i.e., H2O)

Markovnikov's rule: "them that has, gets" (H goes on the C that already has the most H's) addition of non-polar reagents (H2, Br2, etc.) also occurs
R C H C H H + X X R H X C C H X H

C.

Alkynes similar addition reactions as alkenes (stepwise addition can occur)

XY X C R C H Y XY X R X C C Y Y H

D.

Aromatic Hydrocarbons (Benzene and its derivatives) Substitution Reactions (never addition!)
X2 H H X2 H
X = Cl, Br

X H

HNO3
(H+ catalyst)

NO2 H

X ( NOT aromatic ! ) X

Reactions of the Other Functional Groups A. Alcohols R-O-H 1. Oxidation of alcohols:

H R C H H R C O H R' secondary R' R C O H R" tertiary O H
primary

[O]
- "H2"

O R C H
aldehyde

[O]
- "H2"

O R C R'
ketone

[O]

No Reaction

[O] = an oxidizing agent like [Cr 2O7]2-

2. Elimination Reactions of alcohols:

H R C H OH CH2 alcohol

H+

R C H CH2 + H2O

alkene

3. Substitution Reactions of alcohols:

RCH2 OH + H X

- H2O

RCH2

alcohol

X = Cl, Br, I

alkyl halide

B.

Ethers, R-O-R' Ether Synthesis:

R O H + H O R H+
- H 2O

C.

Aldehydes and Ketones 1. Hydrogenation (reduction) of aldehydes and ketones

O R C H
aldehyde

"H2"

OH R C H OH R C H R'
secondary alcohol

H
primary alcohol

O R C
ketone

R'

"H2"

2. Oxidation of aldehydes (very easy!)

O R C H [O] O R C O H

aldehyde

carboxylic acid

D.

Carboxylic Acids 1. Acid + Base Salt of Acids:

O CH3 C O H
acetic acid

NaOH
H2O

O CH3 C O- Na+
sodium acetate

e.g. Soap is a salt of long chain carboxylic acid

O O- Na+
non-polar hydrocarbon "tail" polar "head"

E.

Esters 1. Formation of Esters (from acid + alcohol)

O R C O H + H O R' R

O C O R' + H 2O

2. Saponification of Esters (hydrolysis)

O CH3 C O CH2CH3
ester

NaOH
H2O

O CH3 C + O- Na+ HOCH2CH3

alcohol salt of acid

F.

Amines amines are weak bases, so base + acid salt

RNH 2 + H+ RNH3+

G.

Amides Formed from acid and amine:

O R C O H + H NH2 R O C H N H + H2O