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Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 ) CH 3 butane 2

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Newman projections butane staggered eclipsed stable

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Page 1: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

ReviewAlkanesCnH2n+2

C4H10 a) ethaneb) propanec) butaned) pentane CH3 (CH2) CH3

butane

2

Page 2: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

ReviewAlkanesCnH2n+2

C4H10 a) ethaneb) propanec) butaned) pentane CH3 (CH2) CH3

butane

2

Page 3: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Newman projectionsbutane

staggered eclipsedstable

1

1

2

2

3

3

4

4

http://www.chem.uiuc.edu/clcwebsite/index.html
http://www.chem.uiuc.edu/clcwebsite/index.html
Page 4: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Nomenclature

1 3 4 5 6 7

heptane

12

21

334 4

5

5

6

6

7

7

heptane heptanebranches branches branches

2

3 2 4

Page 5: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Nomenclature2

1

3 4 5 6 7

2-3-4-5-

methylethylpropylethyl

3,5-diethyl

ethylpropyl

methyl

3,5-diethyl-2-methyl -4-propylheptane

Page 6: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkaneslinear alkanesbranched alkanes

cycloalkanes closed rings CnH2n

bond angle = 60o tetrahedral angle = 109o

very unstable

propane

CnH2n+2

1

23

cyclo

Page 7: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkaneslinear alkanesbranched alkanes

cycloalkanes closed rings CnH2n

bond angle = 60o tetrahedral angle = 109o

very unstable

propane

CnH2n+2

1

23

cyclo

Page 8: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclobutane

bond angle = 88o

tetrahedral angle = 109o

unstable

Page 9: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclobutane

bond angle = 88o

tetrahedral angle = 109o

unstable

Page 10: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclopentane

bond angle = 108o

tetrahedral angle = 109o

stable

Page 11: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclopentane

bond angle = 108o

tetrahedral angle = 109o

stable

Page 12: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

1,3-dichlorocyclobutane cis- trans-1,3-dichlorocyclobutane

geometric isomers

-

-

Page 13: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclohexane

predicted bond angle = 120o

tetrahedral angle = 109o

stable

Page 14: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Cycloalkanes

cyclohexane

predicted bond angle = 120o

tetrahedral angle = 109o

stable

Page 15: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2
Page 16: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2
Page 17: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

cyclohexane

chair conformation boat conformationstable unstable

axial positionsequatorial positions

crowded only Hlarger groups

http://www.chem.uiuc.edu/clcwebsite/Webcoursespage.html
Page 18: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

cyclohexane

cis- cis-1,2-dimethylcyclohexane

trans- trans-1,2-dimethylcyclohexane

axial-equatorial

equatorial-equatorial axial-axial

1,2-dimethylcyclohexane

1,2-dimethylcyclohexane

Page 19: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Optical isomerism

bromo

**

bromo trans-

*

*

chloroiodomethane hexane

cyclopentane 1,3-dibromocyclopentaneno C*

C* =Stereocenter4 different substituents

3-methyl

Page 20: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

Alkane Summary1. Alkanes - sp3 hybridized

2. Relatively unreactive Substitution with halogens

Combustion

3. Non-polar IMF = London Dispersion Forces

sizestructure

Page 21: Review Alkanes C n H 2n+2 C 4 H 10 a) ethane b) propane c) butane d) pentane CH 3 (CH 2 )CH 3 butane 2

4. Free rotation around C-C bondsconformations

5. Non-cyclic alkanes - structural isomers

6. Cyclic alkanes - geometric isomerscis-, trans-

7. Alkanes - optical isomersstereocenters C*


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