Chapter 2: Alkanes and Cycloalkanes

Chapter 2: Alkanes and Cycloalkanes

CnH2n - . - . ,

. , . , . -- H2C CH2 H2C H2C CH2 H2C CH2 H2 H2C C

CH2 H2C C H2 cyclopropane cyclobutane cyclopentane H2C H2C H2 C C H2 CH2 CH2 cyclohexane

CH3 H3C CH3 methylcyclopentane 1,1-dimethylcyclobutane Br Br Br Br Br

trans-1,2-dibromocyclohexane Br -a C-C . C. CH CH C C C C C

C C C H2 C H2 C 3 2 CH CH CH2 C8 H16 CH3

: . (a) (b) (c) (d) : . (IUPAC) IUPAC) .

Bridgehead carbons (Hydrindane) (Decalin) A one-carbon bridge (Norbornane) : .

: - . Newman- : H . H H H H H

: - . H H H H HH

To . . 12.6 kJ (IUPAC) 3.0 kcal/mol) +12.6 kJ/mol

: C-C-C 109.5 60. To : 6 . 116 kJ (IUPAC) 27.7 kcal)/mol. H H H H H H

. . 110 kJ (IUPAC) 26.3 kcal)/mol.

, . . 42 kJ (IUPAC) 6.5 kcal)/mol. : . all bond C-C-C bond angles are 110.9. all bonds on adjacent carbons are staggered.

, H . , . C-H . : 1 4 . C-H (IUPAC) H ).

27 kJ (IUPAC) 6.5 kcal)/mol. 41.8 kJ (IUPAC) 5.5 kcal)/mol . 6.3 kJ (IUPAC) 1.5 kcal)/mol . ,

. : . . . Cis,trans :

(IUPAC) ) (IUPAC) 5). 1,2- H H H H H H3 C H H HH3 C H

CH3 H H H H CH3 CH3 cis-1,2-Dimethylcyclopentane H

H CH3 H3 C H CH3 trans -1,2-Dimethyl cyclopentane 1,4- H3 C H

H H CH3 H3 C CH3 H CH3 CH3 H3 C H3 C trans

-1,4-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane CH3 CH3 H3 C CH3 The more stable chair conformation of each trans-1,4-

14.5 kJ/mol CH H 3 H H H3 C CH3 CH3 (less stable)

H (more stable) cis-1,4- H H CH3 H H3 C H CH3 are

conformations of equal stability CH3 H H A B H trans-Decalin H

H H A B H cis-Decalin H one carbon bridge between carbons

14 1 and 4 of the six-m embered ring 1 6 2 5

3 4 (a) O 1 1 4 1 2 3 5

4 (b) 6 (c) 4 Cam phor codeine

morphine cocaine A. : 1. 2. a) 3. ( ) () A. : H2, Ni

Br Br Sn, HCl Mg; then H2O B. () Br-CH2CH2CH2CH2CH2-Br + Zn : 1.

Cl2, heat Cl + HCl 2. 4. : H2, Ni, 80o CH3CH2CH3 Cl2, FeCl3 Cl-CH2CH2CH2-Cl H2O, H+ CH3CH2CH2-OH conc. H2SO4 CH3CH2CH2-OSO3H

HI CH3CH2CH2-I

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