Fl03Exam3Ques - Page Points 1 2 3 4 5 6 7 8 9 10 11 Total T...

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10 9 8 7 6 5 4 3 2 (10) (16) (22) (18) (27) (21) (21) (23) (15) (20) (15) (208) 11 Total T Score 1 Page Points
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Signature_________________________ Pg 1 _____________(10) 1. (10 pts) Circle all the True statements. (Do not circle any false statements) You may notice that many of these resemble rules of the day! A.) E2 reactions involve an antiperiplanar arrangement of a hydrogen atom and leaving group in the key intermediate. B.) E2 reactions involve an antiperiplanar arrangement of a hydrogen atom and leaving group in the transition state. C.) An S N 2 reaction on a primary alkyl halide has a lower overall energy barrier compared to a S N 1 reaction on a primary alkyl halide, because in an S N 2 reaction the nucleophile actually assists in breaking the carbon leaving group bond, while in an S N 1 reaction the carbon leaving group bond must break on its own. D.) For cyclohexyl halides , the requirement for an anti-periplanar transition state geometry in an E2 reaction means that the halide leaving group must be axial, never equatorial. E.) Alkenes are more stable with more alkyl groups attached. F.) Polar protic solvents cannot take part in hydrogen bonding. G.) H-bonding due to the OH group makes alcohols "sticky" so they have high boiling points and alcohols with three or less carbons dissolve completely in water. H.) The OH group is not a leaving group, but several reactions involve the conversion of the OH group into a good leaving group , followed by a substitution or elimination reaction. I.) Primary and secondary alcohols react with PBr 3 and SOCl 2 to give alkyl bromides and alkyl chlorides, respectively, via a mechanism involving a carbocation intermediate. J.) Alcohol dehydration is just the functional reverse of acid-catalyzed alkene hydration becuase the process is actually an equilibrium, the position of which depends on the reaction conditions.
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CH 3 C CH 3 CH 3 C H CH 3 H H C H H C H CH 3 CH 3 Br Br Br Br Signature_________________________ relative rank: CH 4 CH 2 CH 3 Pg 2 _____________(16) CH 3 2. (4 pts total) For the following compounds, rank them in order of most to least reactive with Br radicals in a free radical halogenation reaction, with a 1 under the most reactive and a 4 under the least reactive . relative
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This note was uploaded on 09/13/2008 for the course CH 310M taught by Professor Iverson during the Fall '05 term at University of Texas at Austin.

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Fl03Exam3Ques - Page Points 1 2 3 4 5 6 7 8 9 10 11 Total T...

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