Answer key to Practice Problems for Exam 3

Answer key to Practice Problems for Exam 3 - Chapter 8...

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Chapter 8 (Alkenes: Addition Reactions) 1. Predict the major products of the following reactions. Show the mechanisms for the reactions by drawing the flow of electrons using precisely curved arrows. H 2 SO 4 /H 2 O (or H 3 PO 4 /H 2 O) (HI/HCl) HB r H 2 C H S O O O HO H H 2 O CH 3 O H H CH 3 OH H 2 O H 2 C H Br - CH 3 Br 3 o C + 3 o C + more stable carbocation (Markovnikov rule) 2. Predict the major products of the following reaction. Show the mechanism for the reaction. HBr CH 3 CH 2 O-OCH 2 CH 3 ROOR (peroxide) H 3 CH 2 CO OCH 2 CH 3 r H 3 CH 2 CO H 3 CH 2 COH Br Br Br more stable radical (anti-Markovnikov) Br H Br H 1
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3. Predict the major products of the following reactions, and include stereochemistry where applicable . Give the mechanisms for the reactions. Br 2 H 2 O i) Hg(OAc) 2 / CH 3 OH ii) NaBH 4 Br 2 CCl 4 (solvent) i) Hg(OAc) 2 / H 2 O ii) NaBH 4 Br 2 CH 3 OH Hg OAc Backside attack of Nu - at more substituted carbon OH Hg OAc H 2 O CH 3 H H 2 O OH Hg OAc CH 3 OH H CH 3 NaBH 4 + enantiomer OCH 3 H CH 3 + enantiomer Br Br - Br Br CH 3 + enantiomer Br HOCH 3 Br H 2 O OH Br CH 3 + enantiomer OCH 3 Br CH 3 enantiomer + Hg OAc CH 3 OH OCH 3 H CH 3 H CH 3 OH deprotonation depronation depronation -H 3 O + 4. Give the major products of the following reactions. O 3 (CH 3 ) 2 S i) BH 3 /THF ii) H 2 O 2 , OH - /H 2 O HB H 2 H BH 2 H OH concerted/syn addition cleave & add oxygen H H O O ketone aldehyde + enantiomer Ozonolysis "add to less hindered carbon" (anti-Markovnikov) 2
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5. Give the major products of the following reactions. Include Stereochemistry concerted/syn addition H 2 /Pd PhC O 3 H or MCPBA Os O 4 , H 2 O 2 KMn O 4 OH - /H 2 O CH 2 N 2 or CH 2 ZnI 2 CHBr 3 KOH H H :CBr 2 (carbene) :CH 2 C Br Br CH 2 OH OH OH OH O
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Answer key to Practice Problems for Exam 3 - Chapter 8...

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