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: C≡C H H
H H H H C C
C C H C C H aromatic: H C C H
H C C H
3 H H sp C C 2
sp
H H 2
sp sp H H
3
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 CH4 C2H6 C3H8 C4H8 C6H6
condensed
CH4 CH3CH3 CH3CH2CH3 CH3CH2CH=CH2
structural formula
H H
H H H H H H H H H C C
structural formula H C H H C C H H C C C H H C C C C H C C H
(Lewis) H C C
H H H H H H H H H
H H

line structure –––

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 9 8
bond (σ only), but not a C=C double (σ + π)! 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):
CH3(CH2)3CH3 CH3CH(CH3)CH2CH3 C(CH3)4
pentane 2-methylbutane 2,2-dimethylpropane
functional group position CH3(CH2)2OH OH CH3CH(OH)CH3
OH
(positional isomers): 1-propanol 2-propanol

functional group type CH3CH2OH CH3OCH3

ethanol dimethylether
(functional isomers):

• Stereoisomers: isomers that have the same connectivity, but differ in the B B
spatial arrangement of atoms. There are two classes: D A A D
• Geometric isomers: stereoisomers that differ CH3 CH3 CH3 H
C C
C C C C
in the relative orientation of substituents H H H CH3
not
super- B
e.g. cis- and trans-alkenes cis-butene trans-butene imposable!

• Enantiomers (or optical isomers): C

D
A

stereoisomers that are chiral, non-superimposable on a mirror image (Eğe Ch6)

Organic Functional Group List
Functional IUPAC Name
Compound Prefix/Suffix Example
Group (Common Name)
R-H alkane -ane CH3CH3 ethane

C C alkene -ene H2C=CH2 ethene (ethylene)

C C alkyne -yne HC≡CH ethyne (acetylene)

R-X haloalkane halo- CH3Cl chloromethane

-ol
R-OH alcohol CH3OH methanol
(hydroxy-)
-amine ethylamine
R-NH2 amine CH3CH2NH2
(amino-) aminoethane
ether
R-O-R ether CH3OCH3 dimethyl ether
(alkoxy-)
O O ethanal
C aldehyde -al
R H CH3CH (acetaldeyde)
O O propanone
C ketone -one
R R CH3CCH3 (acetone)
O
O ethanoic acid
R C carboxylic acid -oic acid
O H
CH3COH (acetic acid)
O
O methyl ethanoate
R C ester -oate
O R CH3COCH3 (methyl acetate)
O
O ethanamide
R C amide -amide
NH2 CH3CNH2 (acetamide)
R = alkyl group, an unfunctionalized saturated chain; X = halogen

Organic Common Names

H H O
O
ethylene C C formaldehyde acetaldehyde CH3CH
HCH
H H
O O
acetylene H C C H formic acid acetic acid CH3COH
HCOH
O
benzene phenol OH acetone CH3CCH3
O
toluene aniline NH2 benzaldehyde CH

O
xylene styrene benzoic acid COH