W03 Alkanes Cycloalkanes

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reaction scheme of alkanes and cycloalkanes. • mechanism of S. R reactions. • thermodynamics of halogenation reactions. • selectivity of radical halogenation.
Organic chemistry I Zdeněk Friedl

Chapter 3

Alkanes and cycloalkanes

Solomons & Fryhle: Organic Chemistry 8th Ed., Wiley 2004

Alkanes and cycloalkanes

• • • • • • • • • •

isomers structure of alkanes and cycloalkanes conformation reaction scheme of alkanes and cycloalkanes mechanism of SR reactions thermodynamics of halogenation reactions selectivity of radical halogenation regioselectivity of SR reactions structure and stability of alkylradicals stereochemistry of SR reactions

2

The basic classification of isomers

3

Coordination isomers

4

Structure and spatial models of ethane

5

Spatial models of butane and 2-methylpropane

6

The free rotation around the C-C σ-bond in ethane

7

The Newman and perspective projection

8

The ap vs. sp conformation of ethane

9

The ∆Epot energy change at rotation around the C-C bond in ethane

10

Conformers of butane formed at rotation around the C2-C3 bond

11

The ∆Epot energy change accompanying rotation around the C2-C3 bond in butane

12

The structure and deformation of σ-bond orbitals in the molecule of cyclopropane

13

Heats of combustion vs. ring strain of cycloalkanes

14

The CHAIR and BOAT conformers of cyclohexane

15

The ∆Epot energy change accompanying inversion of the chair conformers of cyclohexane

16

Cis and trans isomers of dimethylcyclohexanes

17

The reaction scheme of alkanes and cycloalkanes

ER

SR

R CH CH2 H H AR

SR

18

SR

Thermodynamics of halogenation reactions of alkanes

19

SR

A mechanism for the radical chlorination of ethane

20

SR

The REGIOSELECTIVITY of radical chlorination and bromination

21

The sp2 hybridization of methyl radical

22

The order of thermodynamic stability of alkylradicals + I effect (HYPERKONJUGATION) of methyl groups

23

The comparison of thermodynamic stability of 1°, 2° and 3° radicals

24

The ΔEa energy change as a measure of selectivity of radical chlorination and bromination

25

The stereochemistry of chlorination of pentane at the C2 atom

26

Basics of organic nomenclature and synthesis

27

Basics of conformational analysis

28