Hydrocarbons

SCH4U - Hydrocarbons

Organic Chemistry
2

Back in the day (1769), people thought organic compounds

could only be isolated from living organisms. Hence the name, organic chemistry. Later (1824), it was discovered that organic compounds can also be synthesized in a lab. Organic chemistry = study of carbon-based compounds

Largest field of chemistry 107 compounds known so far; 90% of them are organic in nature Foundation of biochemistry Drugs, plastics, adhesives, clothes, high-tech electronic, paints, building materials, artificial sweetenersetc.

SCH4U - Hydrocarbons

So Whats so Special about Carbon?

3

It bonds strongly to itself!

can make long chains or ring structures can bond using single, double or triple bonds It bonds strongly to lots of other things too! H, N, O, S, halogens, etc. Remember Carbon has 4 valence electrons Therefore every carbon can only form 4 bonds with other molecules Think of Carbon as chemistrys Lego
SCH4U - Hydrocarbons

it

Hydrocarbons
4

Made only of Carbon and Hydrogen

the name, hydrocarbon. Most other organic compounds are derivatives of hydrocarbons.
Hydrocarbons
Aliphatic (non-aromatic) Aromatic (based on benzene ring systems)

Hence

Open-chain (straight chains or branched chains)

Closed-ring (alicyclic)

Saturated
Alkanes C-C bonds SCH4U - Hydrocarbons

Unsaturated
Alkenes C=C bonds Alkynes CC bonds

Overview of molecules to study this unit

alkanes, alkenes, alkynes Dont fall behind! aromatics Theres a lot of alcohols, ethers new material! aldehydes, ketones carboxylic acids, esters amines, amides addition and condensation polymers

Alkanes and their Properties

6

General formula CnH2n+2 (remember this!!!) Alkanes are saturated hydrocarbons

Saturated means each Carbon bonds to 4 other atoms. There are no double or triple bonds in alkanes

Nonpolar (aka hydrophobic aka immiscible in water)

Therefore intermolecular attractions are London forces

Alkanes with low molecular masses have low melting and

boiling points. increase mass/length increase melting/boiling point (because increased surface area provides more opportunity for London forces to act)

Representation of Hydrocarbons
Molecular formula: C4H10 Structural diagram: Condensed formula:
H H H H C H H C H H C H H C H H H H C H C H C H H C H H

butane

2-methylpropane

CH3CH2CH2CH3 and CH3CH(CH3)CH3 atoms attached to carbon are placed on right Line Notation: carbon atoms in chain written in a zigzag manner and connected by straight lines to depict the tetrahedral bond angle single CH3CH2CH2CH3 CH3CHCH3CH3 bonds

Naming Alkanes (CnH2n+2)

Meth

methane 8 CH4 natural gas Eth ethane C 2H 6 making ethylene Prop propane C3H8 barbecues But butane C4H10 lighter fluid Pent pentane C5H12 solvent Hex hexane C6H14 part of gasoline Hept heptane C7H16 Oct octane C8H18 Non nonane C9H20 Dec decane C10H22 Prefix tells number of carbon Suffix ane tells that it is an alkane (saturated hydrocarbon)
SCH4U - Hydrocarbons

C1 C2 C3 C4 C5 C6 C7 C8 C9 C10

Alkanes Nomenclature
9

1. Identify the longest continuous chain (sometimes called the

main or parent chain) of carbon atoms and name it as usual.

2. Identify any branches that are present and name them. Use

the normal prefixes to name the branches, but remember to use the -yl suffix (i.e. methyl, ethyl, butyl, propyl)
3. Then number the main (parent) chain so that the first

carbon at which branching occurs is the lowest number

4. When more than one branch is present, the branches are

listed in alphabetical order (prefixes like di, tri, tetra and sec, iso, tert are not included in alphabetical order)
SCH4U - Hydrocarbons

Naming and Drawing Alkanes

10

2
1 3

4
5

2- methyl pentane

3-ethyl-2,2-dimethylhexane

Why does 1-methylpropane not exist?

because that would be butane!!

SCH4U - Hydrocarbons

propyl and butyl alkyl groups

two isomers of the propyl group
the coloured bond indicates where the group is
attached to the larger molecule.
H H C H H C H H C H H H C H C H H C H H

11

n-propyl

isopropyl
CH3 CH CH2

four isomers of the butyl group

CH3 CH3

CH3

C CH3

CH3CH2CH2CH2

CH3

CH2

CH

CH3

butyl

sec-butyl

isobutyl

tert-butyl

Substituted Alkanes (i.e. Haloalkanes)

12

One or more of the Hs is replaced with another atom.

(usually halogens or other alkyl groups)

2-bromobutane

2,2-dibromobutane

1,3,5-triiodoheptane
SCH4U - Hydrocarbons

Examples
13

CH2CH3 CH3 CH CH3 CH CH3 C CH3

CH3

4-ethyl-2,3,4-trimethylhexane
CH3
CH3 CH CH CH3 CH3 C CH3 CH CH3 CH2 CH2 CH3

CH2

2,3,4,4,5-pentamethyloctane

CH3
CH3 CH2 CH2

CH
CH

CH3
CH CH2 CH2 CH2 CH2 CH3 CH3

4-isopropyl-5-propyloctane

Structural Isomers
14

same chemical formula but different arrangement of

atoms Ex. Draw all the isomers of pentane (C5H12)

CH3 - CH2 - CH2 - CH2 - CH3
CH3 CH3 - CH - CH2 - CH3 CH3

CH3 - C - CH3
CH3

Cycloalkanes
15

Cycloalkanes contain one or more rings, each of which has

three or more C-atoms Cycloalkanes can be characterized by the molecular formula CnH2n

C3H6
cyclopropane

C4H8
cyclobutane

C5H10
cyclopentane

C6H12
cyclohexane

Cycloalkane Properties
16

3 and 4 carbon rings are less stable than their straight chain

counterparts due to the strain on the bond angles of the molecules normal bond angles between carbons in alkanes is 109.5o, therefore 3 and 4 numbered rings undergo reactions which tend to open up their rings into straight chains in general, cyclic hydrocarbons show the same reactivity as their open chain counterparts

Naming Cycloalkanes
17

Identify the ring of carbon. Assign the base name. Number the ring beginning with the location which will

result in the lowest possible numbers for the branches. Name each branch and indicate the position by the number of the carbon to which it is attached.

1-methylpropylcyclohexane or sec-butylcyclohexane

11.5 Alkenes (CnH2n)

18

unsaturated hydrocarbons containing at least one

carbon-carbon double bond Physical properties melting and boiling points generally tend to rise as molecular mass increases. melting point irregularities are explained by the free rotation about the single bonds, which affect the packing of molecules

Naming Alkenes
19

1. The parent chain must be an alkene, and thus must 2. 3. 4.

5.

contain the double bond. The number of carbons in the parent chain is indicated by the prefix and the name ends in ene When numbering the C atoms in the parent chain, begin with the end closest to the double bond. The location of the double bond is indicated by the number of the C atom that begins the double bond. The presence and location of multiple double bonds is indicated by the prefixes di-, tri-, etc.

Naming Alkenes
20

CH3 CH2 C CH CH3 CH CH2 CH2 CH3 CH3

4-ethyl-2,3-dimethyl-1-hexene

CH2

CH

CH

CH

CH

CH

CH3

1,3,5-heptatriene

Naming Alkenes
21

4-methyl-2-pentene 2-ethyl-1-butene 1,3-pentadiene 3-chloro-4-methyl-1-hexene

Geometric Isomers (cis/trans)

22

Same chemical properties, slightly different physical properties.

H3C H
H H3C

C=C

CH3 H CH3

cis-2-butene
(B.P. 3.72 oC)

C=C

trans-2-butene
(B.P. 0.88 oC)

11.5 Alkynes (CnH2n-2)

23

Unsaturated hydrocarbons containing at least one

carbon-carbon triple bond Physical properties boiling points generally tend to rise as molecular mass increases. melting point do not increase in a regular manner due to free rotation about the single bonds, which affect the packing of molecules.

1-propyne

Naming Alkynes
24

1. The parent chain must be an alkyne, and thus must 2. 3. 4.

5.

contain the triple bond. The number of carbons in the parent chain is indicated by the prefix and the name ends in yne When numbering the C atoms in the parent chain, begin with the end closest to the triple bond. The location of the triple bond is indicated by the number of the C atom that begins the triple bond. The presence and location of multiple triple bonds is indicated by the prefixes di-, tri-, etc.

Naming Alkynes
25

H H C H

H C H C C

H C H H

2-pentyne
H C CH 3 CH 3

H3C

H C CH 2 CH 2 CH 3

C H2

2,6-dimethyl-4-nonyne

Naming Alkynes
26

1-pentyne 3-ethyl-4,4-dimethyl-1-hexyne

3,4,5-trimethyl-1-heptyne

Aromatic compounds
originally meant odourous now means contains the benzene ring: Benzene:

or

or

CH at each corner!

Physical and chemical properties Many derived from petroleum. Good solvents for many organic compounds. Benzene is used as a solvent in which other organic reactions
take place. Aromatic compounds tend to be toxic. Since vapours are also toxic, use aromatic compounds in a fumehood.

Naming aromatic compounds

Named using benzene or derivatives of benzene (toluene or
phenol) as root of the name.
CH3 OH

benzene

toluene

phenol

naphthalene

Number carbons around ring - use to located groups.

CH3 C2H5 CH3 H3C CH3 H3C CH3

ethylbenzene

1,2-dimethylbenzene

1,3-dimethylbenzene

1,4-dimethylbenzene

ortho, meta, and para

Three prefixes to designate three possible arrangements of
disubstituted benzenes Trivial names are based on prefixes.
1
ortho to 1 (o)

Examples:
NO2

NO2

Cl

Cl

Cl

CH meta to 1 3 (m)

Br

m-dinitrobenzene

p-dichlorobenzene

para to 1 (p) p-chlorotoluene

Cl

Cl

CH3

Br

CH3

NO2

-dichlorobenzene

p-chlorotoluene

4-bromo-2-nitrotoluene

More examples:
I

1)

2)
Cl CH3

3)
Br I

Br

Br

o-dibromobenzene
4)
Br NO2

p-chlorotoluene
5)
I

5-bromo-1,2,3-triiodobenzene
6)
Cl CH3

CH3

NO2

4-bromo-2-iodo-6-nitrotoluene

m-diiodobenzene

4-chloro-2-nitrotoluene

N.B. The substituent that gives the compound its base name is placed at carbon 1

The phenyl group

Benzene ring can also be the attached branch, -C6H5 and is
called a phenyl group Example: 4-phenyl-3-propyl-1-hexene
CH2 CH2 CH CH CH2 CH

CH3 CH2 CH3

Practice
32

p.15 #1-2 p.18 #3-6 p.21 #7-8 p.22 #1-4

SCH4U - Hydrocarbons