CHAPTER 3: Families of Carbon Compounds

Hydrocarbons: Compounds that only contain Carbon and Hydrogen


 Alkanes: hydrocarbons that contain only C-C and C-H single
bonds. Molecular formula: CnH2n+2 n = 1,2,3,...

Mol. Formula No. of constitutional Names

Isomers (Parent name in bold)
CH4 1 Methane
C2H6 1 Ethane
C3H8 1 Propane
C4H10 2 Butanes
C5H12 3 Pentanes
C6H14 5 Hexanes
C7H16 9 Heptanes
C8H18 18 Octanes
C9H20 35 Nonanes
C10H22 75 Decanes

Constitutional isomers:
The number of isomers increases dramatically as the number of
carbon atoms increases.
Example: C4H10
CH3

CH3 CH2CH 2CH3 CH

3CHCH 3
butane isobutane
straight-chain alkane branched alkane

 Cycloalkanes: Molecular formula: CnH2n n=3, 4,....

cyclopropane cyclobutane cyclopentane cyclohexane

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 Alkenes: Unsaturated hydrocarbons that contain a C=C bond
with Molecular formula: CnH2n n = 2, 3, 4,..
CH2 CH2 CH3CH CH2
ethene propene
(ethylene) (propylene)

Cis-Trans Isomers: Compounds that have the same

molecular formula, same connectivities but different
arrangement in space.

CH3 CH3 CH3

CH CH CH CH
CH3

cis-2-butene trans-2-butene

Alkynes: Unsaturated hydrocarbons that contain a C≡C bond

with Molecular formula: CnH2n-2 n = 2, 3, 4,....

CH CH CH3C CH
ethyne propyne
(acetylene)

Aromatic Compounds: Hydrocarbons related to benzene

benzene naphthalene anthracene

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 IUPAC (International Union of Pure and Applied Chemistry) Nomenclature
Alkyl (R) groups: are obtained by removing a hydrogen atom
from an alkane.
Alkyl groups are named by replacing the “ane” ending of the
parent alkane with “yl”.
Common alkyl substituents:

CH3 CH3CH2 CH3CH2CH2 CH3CHCH3

methyl ethyl propyl isopropyl

CH3CH2CH2CH2 CH3CH2CHCH3
butyl sec-butyl CH3
CH3CCH2
CH3 CH3
CH3CCH3 neopentyl
CH3
CH3CHCH2 tert-butyl

isobutyl

CH2 CH2CH2
CH CH2 CH
CH2 CH2CH2

cyclopropyl cyclohexyl

CH2

phenyl benzyl
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 Degree of alkyl substitution
A primary carbon (1o) is bonded to one other carbon, a
primary hydrogen is bonded to a primary carbon.
A secondary carbon (2o, sec-) is bonded to two other carbons,
a secondary hydrogen is bonded to a 2o carbon.
A tertiary carbon (3o, tert-) is bonded to three other carbons, a
tertiary hydrogen is bonded to a 3o carbon).
A quaternary carbon (4o) is bonded to four other carbons.

H H R R
H C H R C H R C H R C R R = alkyl group
R R R R
1° 2° 3° 4°

Example: Determine the degree of substitution of the carbons in
the following molecules









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 Combination of alkyl groups with heteroatoms:
Replacement of H of an alkane by OH, NH2 or a halogen (F, Cl,
Br, or I) results in an alcohol, amine and alkyl halide, respectively.

Functional group consists of an atom or group of atoms where

most of the chemical reactions occur. They usually contain
multiple bonds or lone pairs of electrons.

Structure of common functional groups:

Contain C-C multiple bonds: R = H or any alkyl group

R R
Alkene C C
R R

Alkyne R C C R

Contain carbon bonded to an electronegative atom: R = alkyl group

Alcohol R OH Ether R O R

Amine R N R' (R', R'' = H or any alkyl group)

R''

Alkyl Halide R X X = F, Cl, Br, or I

Thiol R SH Sulfide R S R

Nitrile R C N

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 Classification of alcohols Classification of alkyl halides

CH3OH methanol CH3X methyl halide

RCH2OH Primary alcohol RCH2X Primary alkyl halide

RCHOH Secondary alcohol RCHX Secondary alkyl halide

R' R'
R'' R''
RCOH Tertiary alcohol RCX Tertiary alkyl halide
R' R'

Classification of amines

RNH2 Primary amine

RNHR' Secondary amine

R''
RN Tertiary amine
R'

Contain a carbonyl group (C=O):

O
Aldehyde R CHO Ketone R C R'
(R = H or any alkyl group) R, R' = alkyl group

Carboxylic Acid R CO2H Ester R' CO2R

(R = H or any alkyl group) R = alkyl group
(R' = H or any alkyl group)
O
Amide R' N C R (R, R', R'' = H or any alkyl group)
R''
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 List all the functional groups in the following molecules:

O

N
HO
O

CN O

NH
Cl

CO2H SH

S
O
HO CHO
OH 




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 Physical properties
Intermolecular forces:
1. Dipole-dipole interactions result from the attraction of a +
end of one polar molecule to the - end of another molecule.
R
R  R  R  R  R
    N
O   O F   F N R
R R
R R R R R
ketones alkl halides tertiary amines

2. Hydrogen bonding. H is attached to a highly electronegative

atom limited to F, N, and O, the rest of the elements do not
form hydrogen bonding.
R
R O R R R N R 
 R 
H O H O H H N H N 
H
      R  R
Hydrogen bonding in alcohols Hydrogen bonding in secondary amines

3. London or Van der Waals dispersion forces occur when

electrons of a nonpolar molecule may momentarily cause an
imbalance of charge distribution in neighboring molecules,
thereby inducing a temporary dipole moment.

   
 

non polar molecules temporary dipoles dipoles disappear

colliding are generated

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 Order of attraction:
H-bonding >> dipole-dipole > Van der Waals

H-bonding: ROH, RNH2, R2NH, RCO2H

Dipole-dipole: RX, ROR, RSR, R3N, RCN, RCO2R, R2C=O, RCHO
Van der Waals: hydrocarbons (pentane, benzene, ethylene,
acetylene, etc.), symmetrical molecules: Br2, CS2, CCl4, BF3,
Cl2C=CCl2

Boiling point (bp): the greater the molecular weight, the greater
the number of electrons, and the greater the Van der Waals forces.

boiling point

pentane 36 0C

hexane 69 0C

heptane 98 0C

Branching lowers the bp because it reduces the area of contact.

boiling point

hexane 69 0C

2-methylpentane 62 0C

2,2-dimethylbutane 50 0C

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 The boiling point of alcohols is higher than alkanes and aldehydes
because alcohols exhibit hydrogen bonding. Molecules with more
than one OH have even higher boiling points.
boiling point

heptane 98 0C

hexanal O 130 0C

1-hexanol OH 158 0C
(hexyl alcohol)

1,5-pentanediol HO OH 242 0C

Primary and secondary amines also exhibit hydrogen bonding.

boiling point
N,N-diethylethanamine
N 89 0C
(triethylamine)

N-propyl-1-propanamine NH 110 0C
(dipropylamine)

1-hexanamine
NH2 132 0C
(hexylamine)

1,5-pentanediamine H2N NH2 179 0C

Boiling point trends summarized:

Intrmolecular forces > Less Branched > More Branched

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 Melting point (mp): in general increases as the molecular
weight increases (as bp).

melting point

propane 188 0C

pentane 130 0C

heptane 90 0C

Symmetry increases the melting point.

melting point
Cl
Cl
1,2,4-trichlorobenzene 17 0C

Cl

Cl
Cl Cl
1,2,3-trichlorobenzene 52 0C

Cl

1,3,5-trichlorobenzene 63 0C
Cl Cl

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 Rigidity increases the melting point.

melting point

octane 57 0C

2,2,3,3-tetramethylbutane 100 0C

The stronger the intermolecular forces the higher the melting point.

melting point

ethylbenzene CH2CH3 95 0C

benzaldehyde CHO 26 0C

benzyl alcohol CH2OH 15 0C

Melting point trends summarized:

Intermolecular forces > More Branched > Less Branched
More Symmetry > Less Symmetry

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 Solubility: ionic and polar compounds dissolve in polar
solvents, on the other hand, nonpolar compounds dissolve in
nonpolar solvents.

Examples of compounds soluble in water:

NH4Cl CO2Na SO3Na

O
ONa OH NH CH3CN

Examples of compounds insoluble in water but soluble in hexane:

F F

CH2CH3 (CH3)4Si F F

F F

Cl Cl
NC CN CBr4 CS2
Cl Cl

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