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13_all_ - 13.1(a What product(s would you expect to obtain...

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13.1 (a) What product(s) would you expect to obtain if propene labeled with 14 C at C1 were subject to allylic chlorination or bromination? (b) Explain your answer. H 2 14 C CHCH 3 + X 2 high temperature or low conc. of X 2 ? (c) If more than one product would be obtained, what relative proportions would you expect? Answer: (a) It will obtain H 2 14 C CHCH 2 Br and H 2 C CH 14 CH 2 Br . (b) high temperature H 2 14 C CHCH 2 Br H 2 C CH 14 CH 2 Br Br 2 2Br Br + H 2 14 C CHCH 3 HBr + H 2 C C H CH 2 H 2 C C H CH 2 H 2 C C H CH 2 Br Br 14 14 14 (c) 50% to 50% 13.2 (a) Write structures corresponding to D, E and F for the carbocation shown. H 3 C H C C H CH 2 (b) This carbocation appears to be even more stable than a tertiary carbocation; how can you expect this? (c) What product do you expect to be formed if this carbocation reacted with a chloride ion? Answer: (a) H 3 C C C CH 2 H H H 3 C C C H H CH 2 E D H 3 C C CH CH 2 H H 1/2 1/2 F (b) Because the positive charge has been dispersed on two carbons, so it is more stable than tertiary carbocation. (c) H 3 C CH C CH 2 Cl H H 3 C C C H H H 2 C Cl and
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