1559T_ch14_259-27511/3/059:27Pa9e263 ⊕ EQA Solutions to Problems.263 cations to exceed resonance-stabilized allylic cations in stability(the reverse of the order for radicals). 32.(a)(CH3)2CHCBr-CH-CH2.(CH,)2CHC-CHCH2Br OH CH; -CHCH2OCHCH3 CH-OCCH (e)Different!S2 not S conditions ⊕ CH CH-SCH: (f)Intramolecular version: H=C CH CH2CH2CH2OH Again,only one product:bond formation at the other end would produce a more strained seven-membered ring. 33.(a CH3 H H (CH3)CH CH-OH (CH3)CH C-C cH 「CH H H c=c (CHa)CH CH produc produc Solutions to Problems • 263 Hyperconjugation, which is at least partially responsible for the tertiary  secondary  primary stabilization order, is more important for cations than for radicals. The effect is large enough for tertiary cations to exceed resonance-stabilized allylic cations in stability (the reverse of the order for radicals). 32. (a) (CH3)2CHCBrOCHPCH2, (CH3)2CHCPCHCH2Br A A CH3 CH3 (b) (c) (d) (e) Different! SN2, not SN1 conditions: (f) Intramolecular version: Again, only one product; bond formation at the other end would produce a more strained seven-membered ring. 33. (a) CH3 C C H product (CH3)2CH CH2OH CH3 C C H (CH3)2CH CH2 CH3 C C H (CH3)2CH CH2 CH3 C C H (CH3)2CH CH2 OH2 Br Br H    product   CH2 CH2CH2CH2OH CH CH CH2 CH2CH2CH2OH CH CH  H CH2 CH O CH2 I CH3 CH3S CH2SCH3 CH3 This is the only product.  O , O OCCH3 CH2OCCH3 CH3 CH2 C CH3 OCH2CH3 CHCH2OCH2CH3 CH CH2 , OH CH3 , OH CH3 1559T_ch14_259-275 11/3/05 9:27 Page 263