FS Practice Exam #2 key

FS Practice Exam #2 key - B, C none C C C B not...

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CEM 251: Practice Exam #2 (total 100 pts) 1. Name the following compounds according to IUPAC rules (3 pts each box) isobutylene O Br OH Cl Br 2. Draw the structures of the following compounds (3 pts each box) O O CH 3 H 3 C 3. Carbocation (10 pts) 4. Substitution (6 pts) C C H 3 C CH 2 CH 3 CH 3 Cl ( Z )-4-methyl-3-heptene A B C Which of the carbocations is secondary? Which of the carbocations is tertiary? Which is the most stable carbocation? For which reactions is it important to consider stability of carbocation (circle correct answer)? S N 1 S N 2 E1 E2 Br Br Br A B C Which of the above halides reacts fastest by S N 1? Which one gives the slowest substitution with CH 3 NH 2 ? Which of the above halides reacts fastest by S N 2? 5. Elimination (4 pts) Cl NaOH E2 major NaOH E2 major Br ( S )-2-methoxybutane 3-bromocyclopentanol 4-bromo-5-chlorohex-1-yne or 4-bromo-5-chloro-1-hexyne 2-ethyl-3-methyloxirane 1-isopropoxy-2-methylpropane or isobutylisopropyl ether ( E )-2-chloro-3-methylpent-2-ene or ( E )-2-chloro-3-methyl-2-pentene
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Unformatted text preview: B, C none C C C B not antiperiplanar 6. Fill in the boxes: Br 2 H 2 O Br 2 CH 3 OH H 2 SO 4 H 2 O D 2 SO 4 BH 3 , NaOH H 2 O 2 H 2 O H 2 SO 4 a.) b.) c.) O d.) Williamson ether synthesis: name reaction one way other way HBr excess heat e.) NH 2 ______________ name the functional group C C H 3 C CH 2 CH 3 CH 3 H Br 2 f.) bromonium ion intermediate, show stereochemistry product of the reaction name the starting material SOCl 2 OH HO g.) H 2 SO 4 h.) CH 3 CH 2 CH 2 OH compound with a very good leaving group CH 3 CH 2 CH 2 CN O alcohol alcohol alcoxide alcoxide halide halide HO NaO Na Na Cl OH ONa Br Cl Br Br ( Z )-3-methyl-2-pentene C C H 3 C CH 2 CH 3 CH 3 H Br Br Br N H OH OH O epoxide NaCN CH 3 CH 2 CH 2 O S O O S Cl O O CH 3 Tosyl chloride (Tos-Cl) Br Br Br OH OCH 3 OH both syn and anti are correct in b. OH H HO D...
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FS Practice Exam #2 key - B, C none C C C B not...

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