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 9) cis 1,2 dimethyl cyclohexane

a)

HC CH, most stable conformation ( every other structure is similar because always one methyl will be in equatorial position and other in axial position)

b)

CH3 CH3 CH3 Br -CH3 Brz. hv

c)

CH3 CH3 CH3 CHF CH3 CH3 CH3 F2 -CH₃ + + hv F

d) Bromination is less exothermic than fluorination. Bromine is less reactive than fluorine and are muchore selective thus only one product is formed. But fluorine is vigourously reactive and forms many produts.

e) The reaction betweem 1 bromo 1, 2 dimethylcyclohexane and hot ethanol follows fist order nucleophilic substitution reaction (S 1) ans well as unimolecular elimination reaction (E1).

f)

CH3 CH2 CH3 hot CH,OH CH3 -OCH 3+ +

mechanism

1

CH3 CH3 CH3 CH3 CH3 CH3 -Br CH3 OCH 3 CH3 CH,OH -OH CH3

E1

CH3 CH3 CH3 CH3 -Br CH2 CH,OH

CH3 CH3 CH3 Нас не „Сн, CH3 -Br 8 CH,OH

The major product is CH3 CH3 according to saytzeff's rule ( According to Saytzeff Rule the elimination will lead predominantly to the olefin in which the double bond is more highly substituted)

g)

CH3 CH3 CH3 R? R Br CH3 CH3 .....OCH 3 CH₃ R hot CH,OH R G S Biz hv

The product is (1R,2R)-1-methoxy-1,2-dimethylcyclohexane

CH3 (4 сна ...OCH3 3 anticlockwise and least priority towards you - R configuration

Hс н CH3 ...ОСН3 clockwise and least priority away from you - R configuration

h)

CH3 CH3 cis 1,2-dimethylcyclohex-1-ene ( the two similar groups are on same side)

CH3 CH2 1-methyl-2-methylidenecyclohexane ( neither cis nor trans)

CH3 CH3 1,6-dimethylcyclohex-1-ene( neither cis nor trans)

i)

CH3 CH3 CH3 CH3 Br NaOCH

ST

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