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Chapter 18 Organic Chemistry IThe Hydrocarbons

18-1 Aliphatic Hydrocarbons

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18-1

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Hydrocarbons

CxHy Aliphatic hydrocarbon

Aromatic hydrocarbon

CH3CH2

CH2

CH2

CH2

CH3

CH2CH3

()

Chemical

Name

Chemical

Formula

Structural

Formula

Line

Structure

Condensed

Structural

Formula

Hexane C6H14CH3CH2CH2CH2CH2CH3

or

CH3(CH2)4CH3

CH3CH2

CH2

CH2

CH2

CH3

()

Line Structure

()

Condensed Structural formula

CH3

CH

CH2

CH2

CH2

CH

CH2

CH3

CH3 CH3

()

Structural formula

CH3(CH2)2C(CH3)2CH2C(CH3) 3 C4H10

()

AlkanesMethane CH4

Ethane CH3CH3

Alkenes

Alkynes

()

~ane cyclo ~ ane

Butane

Methylpropane

()

~ane~ane~yl

()

CH3-

CH3 CH2-

CH3 CH2CH2-

CH3 CH

CH3

CH2

CH3

()

cyclo

1

-

3-Ethyl-hexane

12

3

CH3C(CH3)2CH2CH31 2 3

2,2-Dimethyl-butane

4

()

di-, tri-, tetra-, penta-, hexa-

2,2,3-Trimethyl-butane

1-Ethyl-2-methyl-cyclopentane

()

1

Write the structural formula of5-ethyl-2,2-dimethyldecane

2,3,5-trimethyl-4propylheptane

2-ethyl-1,1-dimethylcyclohexane

()

2Write the name of

()

~ane ~ene

~ane ~yneC

eneyne

1-Pentyne

2-Pentene

1,4-Pentadiene

123

3 12

12

34

()

C

1. functional group suffixes

2. double bonds3. triple bonds4.

prefixes

()

Name the compoundsCH3CH=CHCH3(CH3)2CHCH(CH3)CHClCCH

Write the condensed structural formula for 5-methyl-1,3-hexadiene

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CxHy Isomers

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Structural Isomers?

CnH2n+2 CnH2n CnH2n-2

Draw structural formulas for all the isomeric alkanes of formula

C5H12 3 isomers

C3H6 2 isomers

C4H9Br 4 isomers

()

Geometric Isomers?

Draw structural formulas for all the isomeric alkanes of formula

Write the structure formulas and name all the isomers of the alkenes

C4H8

()

Optical Isomers?

Indicate which of the following molecules are chiral

CH2FCl

CHFClBr

CH3CH(OH) CH3CH3CH(OH) CH2CH3

()

Isomers

Identify each of the following pairs as structural isomers, geometric isomers, or not isomers:

Butane and cyclobutane

Cyclopentane and pentene

andand

and

()

Isomers?

()

()

()

Which compound has the higher boiling point?CH3CH2CH2CH2CH3 or CH3CH2CH2CH3 CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3

()

C-CC-HCnH2n+2 +H2SO4CnH2n+2 +HNO3CnH2n+2 + MnO4-

CH4+2O2CO2+2H2OH = -890 kJ

CH4+Cl2CH3Cl+HClH = -105 kJ

(kJ/mol)

C-C 348

C-H 412

H-Cl 431

Cl-Cl 242

I-I 151

C-Cl 338

O=O 496

()

ClCClCHClClClCHClClCHClClClCHClCHCl

molkJmolkJClClClmolkJClClCHCHClmolkJCHHClCHClmolkJClClCl

gHClgClCHgClgCHheatlight

heatlight

5n Propagatio 4n Propagatio 3n Propagatio

/ 105H / 243H :n Terminatio

/ 109 H 2n Propagatio/ 4 H 1n Propagatio/ 242H Initial

)()()()(

43

322

223

2

332

34

or 2

3or

24

()

EX 18.26

A branched hydrocarbon C6H14 reacts with chlorine in the presence of light to give only two structural isomers with the formulas C6H13Cl.

Write the structure formulas of the hydrocarbon and the two isomeric products.

Do any of the products exist as optical isomers?

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Bond Enthalpies

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Elimination Reaction

dehydrohalogenation of haloalkanes

CH3CH3(g)Cr2O3

CH2 CH2 H2(g)(g) +

Br

CH3CH2O- Na

+

CH3CH2OHCH3CH2OH

NaBr+

at 70

+

()

Electrophilic Addition CH2=CH2 + Br2 CH2Br-CH2Br

CH2=CH2 Br2 electrophile Lewis

Brd-

Brd+ Br+

Br

Br+

Br

Br

Br

()

Ex 18.39

Two structural isomers can result when hydrogen bromide reacts with 2-pentene

Write their structural formulas

What name is given to this type of reaction?

()

Ex 18.41

Write a balanced equation for the reaction of bromocyclohexane with sodium ethoxide in ethanol.

Draw structural formulas of the cyclic reactant and product.

What name is given to this type of reaction?

()

()

OOO O

O

O

O

O

O

O

O

+ 3

Glycerol

Stearic acid

Tristearin, C57H110O6

()

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