SCHEME 13.1: HYDROCARBONS ALKANES 1. (a) (b) (c) (d) (e) (f) 2.

. (a) 2-methylbutane 3-ethyl-2-methylpentane 2,3,3-trimethylhexane 4-isopropyl-3,6-dimethyloctane 5-ethyl-1,2,3-trimethylcyclohexane 1-bromo-3-ethyl-1-methylcyclopentane

Cl H3C (b) CH3 C CH CH3 (c) Br Cl Cl

CH3 CH3

(d)

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SCHEME 13.1: HYDROCARBONS ALKANES 3. (a) pentane < heptane < nonane < decane Molecules with bigger molecular weight (size) have bigger surface area and stronger van der Waals forces. More energy is needed to separate bigger molecules and therefore the boiling point increases with increasing molecular weight. Decane has the highest boiling point because it has the biggest molecular weight (size) while pentane has the lowest boiling point because it has the lowest molecular weight (size). (b) 2,2-dimethylpropane < 2-methylbutane < pentane For molecules with the same molecular weight, branching decreases surface area and van der Waals forces, therefore molecules with more branches or smaller surface area have lower boiling points. 2,2-dimethylpropane is the most branched molecule, therefore it has the lowest boiling point whereas pentane is a straight chain molecule. Therefore it has the highest boiling point. (c) (CH3)2CHCH3 < CH3(CH2)2CH3 < (CH3)4C < CH3(CH2)3CH3 Molecules with higher molecular weight have higher boiling points. Less branched alkanes have higher boiling points. CH3(CH2)3CH3 have the same molecular weight (size) with (CH3)4C but CH3(CH2)3CH3 is straight chain molecule so it has the highest boiling point. While (CH3)2CHCH3 has the lowest boiling point because it has the lowest molecular weight (size) and the most branched molecule. 4. Butane is insoluble in water because it is a non-polar compound and cannot form hydrogen bond with water, however butane is soluble in nonpolar solvent like benzene because it can form intermolecular van der Waals forces. 5. (a) (b) C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g) C3H8(g) + 7/2O2(g) 3CO(g) + 4H2O(g) or C3H8(g) + 2O2(g) 3C(s) + 4H2O(g) 6. (a) (b) (c) (d) Free radicals substitution reaction. Provide energy for the homolytic cleavage. CH3CHBrCH3 major product CH3CH2CH2Br minor product Initiation step
Br Br UV Br + Br

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SCHEME 13.1: HYDROCARBONS ALKANES Propagation step

CH3 Br + H C H CH3 H Br +

CH3 C H CH3

CH3 H3C C H +

CH3 Br H3C C H Br

Br

Br

Termination step

Br

Br

Br

Br

CH3 H3C C H +

CH3 C H CH3 H3C

CH3 C H

CH3 C H CH3

CH3 H3C C H + Br H3C

CH3 C H Br

(e) (f)

The reddish-brown colour of bromine is decolourised. The reddish-brown colour of bromine is unchanged.

OBJECTIVE QUESTIONS 1. 2. 3. 4. 5. C C A C B 6. 7. 8. 9. 10. C C D D B

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