Organic Compounds: hydrocarbons and derivatives

just C and H

C, H, N, O, X, etc

Hydrocarbons: just C and H atoms

alkane: C-C
alkene: C=C alkyne: CC
H

H H

C C

H C C H
H H

sp

sp

H
C C

H C C H

aromatic:

H C

C H
C C

sp

sp

Alkanes are saturated: all C atoms are sp , with four bonds to four atoms, CnH2n+2
All other hydrocarbons are unsaturated: multiple bonds or rings, fewer than 2n+2 H atoms
Representing Organic Compounds
chemical formula
condensed
structural formula
structural formula
(Lewis)

CH4

C2H6

C3H8

C4H8

CH4

CH3CH3

CH3CH2CH3

CH3CH2CH=CH2

H H

H H H

H C H

H C C H

H C C C H

line structure

H H

C6H6

H H

H C C C C
H H H

H H H

H
C C

H C

C H
C C

Line structure: each C-C bond is a line, H atoms

on C are omitted always four bonds to C!
Note: groups can rotate about a C-C single
bond ( only), but not a C=C double ( + )!

same molecule

different molecules

Isomers
Isomers: compounds with the same molecular formula, but different structures
Structural Isomers: isomers that differ in the bonding arrangement and connectivity of
atoms. Such isomers can differ in terms of:
carbon backbone
(skeletal isomers):
functional group position
(positional isomers):
functional group type
(functional isomers):

CH3(CH2)3CH3
pentane
OH

CH3CH(CH3)CH2CH3
2-methylbutane
CH3(CH2)2OH
1-propanol

CH3CH2OH
ethanol

C(CH3)4
2,2-dimethylpropane
OH

CH3CH(OH)CH3
2-propanol

CH3OCH3
dimethylether

B
B
Stereoisomers: isomers that have the same connectivity, but differ in the
spatial arrangement of atoms. There are two classes:
D
D
A A
C
C
CH3 CH3
H
Geometric isomers: stereoisomers that differ CH3
C C
C C
not
in the relative orientation of substituents
H
H
H
CH3
superB
imposable!
cis-butene
trans-butene
e.g. cis- and trans-alkenes
C
A
Enantiomers (or optical isomers):
D
stereoisomers that are chiral, non-superimposable on a mirror image (Ee Ch6)

Organic Functional Group List

Functional
Group

Compound

Prefix/Suffix

Example

IUPAC Name
(Common Name)

R-H

alkane

-ane

CH3CH3

ethane

C C

alkene

-ene

H2C=CH2

ethene (ethylene)

C C

alkyne

-yne

HCCH

ethyne (acetylene)

R-X

haloalkane

halo-

CH3Cl

chloromethane

R-OH

alcohol

R-NH2

amine

R-O-R

ether

-ol
(hydroxy-)
-amine
(amino-)
ether
(alkoxy-)

CH3OH

methanol

CH3CH2NH2

ethylamine
aminoethane

CH3OCH3

dimethyl ether

aldehyde

-al

O
CH3CH

ethanal
(acetaldeyde)

ketone

-one

O
CH3CCH3

propanone
(acetone)

carboxylic acid

-oic acid

O
CH3COH

ethanoic acid
(acetic acid)

ester

-oate

O
CH3COCH3

methyl ethanoate
(methyl acetate)

amide

-amide

O
CH3CNH2

ethanamide
(acetamide)

O
R

O
R

O
R C

O H

O
R C
O R
O
R C

NH2

R = alkyl group, an unfunctionalized saturated chain; X = halogen

Organic Common Names

H

ethylene

formaldehyde

C C
H

acetylene

H
H

H C C H

formic acid

acetaldehyde

HCH
O
HCOH

benzene

phenol

OH

toluene

aniline

NH2

xylene

styrene

acetic acid
acetone

O
CH3CH
O
CH3COH
O
CH3CCH3
O

benzaldehyde

CH
O

benzoic acid

COH