1559T_ch12_220-24611/02/0521:55Pa9e232 EQA 232.Chapter 12 REACTIONS OF ALKENES H CH C=CCH.CH All chiral products will be formed as racemic mixtures. (a)CH;CH2CH(CH)CH2CH:CHs (b)Syn addition:CH3CH2" c-0 H CH,CH H OH (c)Syn:CHaCHz -C H CHCH (d)CH,CH.CCI(CH)CHCH.CH (e)CH,CH2CBr(CH,)CH2CH,CH, (f)CHaCH2CH(CHa)CHBrCH2CHa(mixture of stereoisomers) (gCH.CH.CI(, (h),(p)CH,CH,C(OH(CH)CH,CH,CH, (i)Ami adition:CH.CH CH:C (j)Anti:CH:CH2 (k)Anti:CHCH cHcH CH:Br (l)CH,CH2CH(CH3)CH(SCH)CH2CH3(mixture of isomers) OHOH ()CHCH C.CH 0 0 (o)CH.CH.CCH,+CH.CH.CH 40. Starting compound is All chiral products will be formed as racemic mixtures. (a) CH3CH2CH(CH3)CH2CH2CH3 (b) Syn addition: (c) Syn: (d) CH3CH2CCl(CH3)CH2CH2CH3 (e) CH3CH2CBr(CH3)CH2CH2CH3 (f ) CH3CH2CH(CH3)CHBrCH2CH3 (mixture of stereoisomers) (g) CH3CH2CI(CH3)CH2CH2CH3 (h), (p) CH3CH2C(OH)(CH3)CH2CH2CH3 (i) Anti addition: (j) Anti: (k) Anti: (l) CH3CH2CH(CH3)CH(SCH3)CH2CH3 (mixture of isomers) (m) (n) Syn: O O B B (o) CH3CH2CCH3  CH3CH2CH (q) Mixture of E  Z isomers of starting compound, and E  Z isomers of CH3CHPC(CH3)CH2CH2CH3 (which is also trisubstituted) CH3 H C C CH2CH3 CH3CH2 OH OH CH3 H C C CH2CH3 CH3CH2 O CH2CH3 CH3CH2 CH3CH2O C C CH3 Br H CH2CH3 CH3CH2 C C CH3 Cl I H CH2CH3 CH3CH2 C C CH3 Cl Cl H CH2CH3 CH3CH2 H C C CH3 H OH CH2CH3 CH3CH2 H C C CH3 D D CH3 CH2CH3 CH3CH2 H C C 232 • Chapter 12 REACTIONS OF ALKENES 1559T_ch12_220-246 11/02/05 21:55 Page 232