Organic Chemistry – Lecture 2

Review

Alkanes, alkenes, alkynes

Hydrocarbon nomenclature
 Aromatic Compounds

originally meant odourous

now means contains the benzene ring:

or or

CH at each corner!
 Common Benzene Compounds

CH3 NH2 OH

methylbenzene Aminobenzene Hydroxybenzene

(toluene) (aniline) (phenol)
 Naming Benzene Compounds
1,2 C’s 1,3 C’s
are “ortho” are “meta”

NH2 I
1 1
2 NH2 2

3
I
1,2-diaminobenzene 1,3-diiodobenzene
ortho-diaminobenzene meta-diiodobenzene
 Naming Benzene Compounds
1,4 C’s
are “para”

Cl
1
2
1,4-dichlorobenzene
para-dichlorobenzene
3
4

Cl
Naming Benzene Compounds
Use the lowest possible numbers!

Br
4
3
1,2,4-tribromobenzene
2
not 1,3,4-tribromobenzene
1
Br
Br
Naming Benzene Compounds

NO2
4
3

2
2-bromo-1,4-dinitrobenzene
1
Br
NO2
substituents are in alphabetical order
Naming Benzene Compounds

OH
Cl Cl pentachlorophenol
(no numbers necessary)
Cl Cl
Cl
As a group, benzene = “phenyl”

CH3 methylbenzene
or (toluene)

phenylmethane
As a group, benzene = “phenyl”

2 1
3

3-phenyl cyclohexene

(smell of new carpets!)

 Functional Groups

…an atom or group of atoms with a characteristic

chemical behaviour

…regardless of the rest of the molecule

Functional Groups
Alkyl halides
Alcohols
Ethers
Amines
Aldehydes
Ketones
Carboxylic acids
Esters
Amides
Nitriles
 1. Alkyl Halides

R-X
Alkyl group
Halogen: F, Cl, Br or I
1. Alkyl Halides

CH3Br

methylbromide

bromomethane
 1. Alkyl Halides

1 5

4-fluoro-2-methylpentane
1. Alkyl
Halides
 2. Alcohols
-R-OH

CH3OH methanol
CH3CH2OH ethanol

HO OH
C=C H ethylene glycol
H
 2. Alcohols
OH phenol
HO

menthol
cholesterol
(3S,8S,9S,10R,13R,14S,17R)-10,13-
dimethyl-17-[(2R)-6-methylheptan-2-yl]-
2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-
HO 1H-cyclopenta[a]phenanthren-3-ol
Reactions of Alcohols
formation of ethers
CH3CH2-OH + HO-CH2CH3
heat, H2SO4

CH3CH2 - O - CH2CH3
+
H2O
 3. Ethers

general formula R - O - R
named for R, R
CH3CH2 - O - CH2CH3 diethyl ether

O t-butylmethyl ether
 3. Ethers
low Tm, Tb

CH3CH2OCH2CH3

diethyl ether Tb = 34oC

“ether”
No H–bonds!
 4. Amines
R3
general formula N
R1 R2

N N N
R1 H R1 H R1 R3
H R2 R2
primary secondary tertiary
 Naming Amines
CH3NH2 methylamine
(CH3)2N H dimethylamine
(CH3CH2)3N triethylamine
phenylamine
NH2 (aminobenzene) (aniline)
diaminopropane
H2N(CH2)3NH2 (putrescine)
 Other Amines
morphine, codeine, cocaine,
novacaine
O =
C NH2
HO
paraamino benzoic acid (PABA)
 5. Aldehydes
H
general formula -C=O
always occurs
at end of a chain aldehydes contain the
carbonyl (C=O)group
 Naming Aldehydes
O O O

=
C C C
H H H3C H H
methanal ethanal phenylmethanal
(formaldehyde) (acetaldehyde) (benzaldehyde)
resins, perfumes, flavors, artificial
preservative plastics almond flavor
 Naming Aldehydes

O O

=
CH3CH2CH2C CH=CH-C

=
H H

butanal 3-phenylpropenal

(rancid butter) cinnamaldehyde

 Naming Aldehydes

4 3 2 1 O

=
CH3CHCH2C
H
Cl the carbonyl
carbon is number 1
3-chlorobutanal
 Making Aldehydes

oxidation of primary alcohols

oxidation H
CH3CH2OH (air, 300 C)
o
H3CC=
O
ethanol ethanal