Steroid Reaction Mechanisms by D. N. Kirk, M. P. Hartshorn

By D. N. Kirk, M. P. Hartshorn

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0]decane bicyclo[3 . 2] decane 3-36 HO - CH 2CH 2CH 3 HO - CH 2CH 2CH 2CH 2CH 3 HO - C H2CH 2CH 2CH 3 HO - CH 2CH 2CH 2CH 2C H 2CH 3 3-37 (a) (b) (c) (d) 3 -ethyl-2,2,6-trimethylheptane 3-ethyl-2,6,7-trimeth y loctane 3 ,7 -diethyl-2,2,8-trimethyldec ane 2-ethyl-l, l -di methylcyclobutane (e) (f) (g) (h) bicyclo[4 . 0] h eptane cis- l -ethyl-3-propylcyc lopentane ( 1 , I-di ethylpropyl)cyclohexane cis-l-ethyl-4-isopropylcyclodecane 3 - 3 8 There are ei ghteen i somers of C sH IS. Here are ei ght of them.

Large net dipole C� �CI H / C == C '" H net dipole 1 31 = 0 (hydrogen bonds shown as wavy bond) 2- 1 7 (a) (CH3hCHCH2CH2CH(CH3h has less branching and boils at a higher temperature than (CH3hCC(CH3h . (b) CH3(CH2)sCH2 0 H can form hydrogen bonds and will boil at a much higher temperature than CH3(CH2) 6CH3 which cannot form hydrogen bonds. (c) HOCH2(CH2)4CH2 0 H can form hydrogen bonds at both ends and has no branching; it will boil at a much higher temperature than (CH3hCCH(OH)CH3 . Cd) (CH3CH2CH2hNH has an N-H bond and can form hydrogen bonds; it will boil at a higher temperature than (CH3CH2hN which cannot form hydrogen bonds.

Carefully check your answers to AVOID DUPLICATE STRUCTURES . ) (a) n-hexane 2,2-di methylbutane 2-methylpentane 3-methylpentane 2,3 -di methylbutane 45 3-5 continued (b) � n-heptane 2-methylhexane T� 3 , 3 -di methylpentane 2,3-di methylpentane 2 ,2-dimethylpentane 3-methylhexane �� 2,4-di methylpentane 3 -ethylpentane 2,2,3 -trimethylbutane 3-6 For thi s problem, the carbon numbers in the substituents are indicated in italics. (a) CH3 (b) CH3 1 -CH2CHCH3 -CHCH3 1 (d) 1 2 I-methylethyl common name (c) I = 2 1 -CHCH2CH3 3 2-methylpropyl common name isobutyl isopropyl CH3 2 0/ = /1C CH3 30 l,l- di methylethyl common name = r-butyl or rerr-butyl 3-7 (b) 3 -8 Once the number of c arbons is determined, C nH2n+2 gi ves the formula.

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