Organic Functional Group List [PDF]

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

C C

H C C H H H

sp

H

3

H

2

sp

H C C

H C C H

aromatic:

H C

C H C C

sp

H

H

H

3

2

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)

CH4

C2H6

C3H8

C4H8

CH4

CH3CH3

CH3CH2CH3

CH3CH2CH=CH2

H

H H

H H H

H C H

H C C H

H C C C H

H

line structure

H H

C6H6

H

H H

H

H C C C C H H H

H H H

H C C

H C

H

C H C 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 (σ only), but not a C=C double (σ + π)!

9

8

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 (Eğe 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

HC≡CH

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

C

H

O R

C

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

O

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