andersen237_final_packet_B_key - CHEM238 Final Exam Study...

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CHEM 237B Test # 3 , TA (24) I. True (T) /False (F). The scoring on this section will be + 4 for each correct answer, - 1.5 for each wrong answer. + s-lire, auk& + '. . An increasing proportion of SN1/E1 versus SN2 products at higher temperatures 'V*reflects the fact that the energy required for heterolytic bond cleavage decreases as the temperature is raised. . The relative stabilities of carbocation intermediates account for the addition reaction outcomes that correspond to the application of Markovnikov's rule. 7- . Alkyl shifts that lead to rearranged carbon skeletons in elimination products cannot occur when the E2 mechanism applies. . CH~CECH is 1019 times more acidic than CH3CH=CHz , that makes the alkyne a moderately strong acid like CH3CHzOH. - shl\ m l r t i w r ' b e F- 2 . Secondary alkyl bromides do not undergo S N reactions. (13) . Given the following relative acidities in CH30H - H2Se > H2S > H20, rank the relative nucleophilicities of the following species in DMSO: ,; rpmhz r.l-, , - n u ~ p r ; ~ . Q - - +lPu ~ ~ C I ? + - J b) H20, H2S, and HO- - ffb- 7 H,o 7 HLS a) HO-, HS-, HSe- and NH3 z Nff3 z HS- > Hlr- (10) III. Cis-4-t-butylcyclohexyl bromide reacts with tBuOK/tBuOH about 500 times faster than the trans isomer. Propose the mechanism and explainwhy the cis isomer isomer reacts faster.
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