Organic Compounds: hydrocarbons and derivatives

just C and H C, H, N, O, X, etc

H C C H C H C C
3

Hydrocarbons: just C and H atoms alkane: C-C alkene: C=C alkyne: CC

H H H C C H H H sp
3

H C C H sp
2

H H

H C C H sp

aromatic:

H C H

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) line structure CH4 CH4
H H C H H

C2H6 CH3CH3
H H H C C H H H

C3H8 CH3CH2CH3
H H H H C C C H H H H

C4H8 CH3CH2CH=CH2
H H H C C C C H H H

C6H6

H C C C H C C H

H
H C

H
H

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

C(CH3)4 2,2-dimethylpropane
OH

CH3CH(OH)CH3 2-propanol

CH3CH2OH ethanol

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 R-H
C C
C C

Compound alkane alkene alkyne haloalkane alcohol amine ether aldehyde ketone

Prefix/Suffix -ane -ene -yne halo-ol (hydroxy-) -amine (amino-) ether (alkoxy-) -al -one

Example CH3CH3 H2C=CH2 HCCH CH3Cl CH3OH CH3CH2NH2 CH3OCH3 O CH3CH O CH3CCH3 O CH3COH O CH3COCH3 O CH3CNH2

IUPAC Name (Common Name) ethane ethene (ethylene) ethyne (acetylene) chloromethane methanol ethylamine aminoethane dimethyl ether ethanal (acetaldeyde) propanone (acetone) ethanoic acid (acetic acid) methyl ethanoate (methyl acetate) ethanamide (acetamide)

R-X R-OH R-NH2 R-O-R

O R C O R C O R C R H

carboxylic acid
O H

-oic acid

O R C O R O R C NH2

ester

-oate

amide

-amide

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

Organic Common Names

H H C C H H H C C H

ethylene acetylene benzene toluene xylene

formaldehyde formic acid phenol aniline styrene

O HCH O HCOH

acetaldehyde acetic acid acetone benzaldehyde benzoic acid

O CH3CH O CH3COH O CH3CCH3 O CH O COH

OH

NH2