Organic Chemistry

H C C H

C C

C

CC

C

H H

H

HH

H HO

H

H H

H

H

C C

C

H H

H

H

CC

CH

H

H

H

HH

H

H

Esterification is a reversible reaction.

(De-) Esterification reaction

desterification reaction

H

O

H

O-CC-C

O

+ester

alcohol

carboxyl acid

H

C-C

O

O H

O-C+

Carbons

Halocarbons are organic compounds containing covalently bonded halogens.

C

C

C

H

H

H

H

H

H

H

Cl

1- chloropropane

C

Cl

Cl

Cl

Cl

carbon tetrachloridetetrachloromethane

Halocarbons are usually man-made.

Types of Halocarbons

Alkyl Halide: the halogen is attached to an aliphatic carbon chain - (alkane, -ene, -yne)

Aryl Halide: the halogen is attached to a carbon that is part of an aromatic ring - (benzene)

I

CH2 - CH - CH - CH3

CH3-

-F

The HaloCarbons (Cl, Br, I, Fl)

· Name the halogen as a branch, replacing - ine in the name of the halogen with - o.

· Multiple halogens are listed alphabetically.· All other rules the same (di, tri, lowest number…)

2-bromo-2-methylpropane

CH3 CH3

CH3

C

BrC C

Cl

H

H

H

chloroetheneiodomethaneI CH3

-

1. bromobenzene2. 3-chloro-1-butene3. 1,2 - difluoropropane4. 1-bromo-3,5-diiodobenzene5. 1,2,3 - triiodocyclopentane

CH3

CH3 C H Cl

--l

l

lCH3

lBr

l CH3

I-CH2-C-CH2-CH2-CH3

Brl

Organic Reactions

+ = ?

Substitution Reactions

Halogenation Reactions

H atom replaced on a chain with a halogen group:

R-H + X2 R-X + HX UV light

H-C - C-H + Cl2 H-C - C-Cl + HCl H

H H

H

H H

H Hethene chloroethane

Alkane + Halogen Halocarbon Halogen halide+

halocarbon hydroxide ion

alcohol halide ion

R-X OH R-OH X+ +H2O

Halogen is replaced by hydroxide ions (OH -) to produce an alcohol and a salt.

CH3I + KOH CH3OH + KI

Iodomethane methanol

100◦C

H2O

100◦C

Addition / Elimination

1 + 1 = 2

Esterification reaction

desterification reaction

H

O

H

O-CC-C

O

+ester

alcohol

carboxyl acid

H

C-C

O

O H

O-C+

hydrogenation reaction

+

H

H H

H

H

C C

H

HH

dehydrogenation reaction

H

H H

HC C

alkene

alkane

(alkyne)

(alkene)

hydration reaction

+

HOH

dehydration reaction

alcohol

H

H H

HC C

H

H H

HC C H

O

H

alkene

HBr

alkyl halide

+

H

H H

HC C

H

H H

HC C

alkeneaddition reaction

elimination reaction

BrH

alkyl dihalide

addition reaction

+

elimination reaction

H

H H

HC C

H

H H

HC C

alkene

Cl Cl

Cl Cl