KEY_QUIZ+2-2++51B+W++08

KEY_QUIZ+2-2++51B+W++08 - H 2 O O H H 2 O 1 3 5 5 1 O b...

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CHEM 5lA PRACTICE QUIZ 2 WINTER’08 M. Taagepera Ch.10 - Alkenes, Ch.11 - Alkynes 1. Predict INTERMEDIATES AND PRODUCTS of following reactions (similar to #46, 47, 48). a) If the products will produce ENANTIOMERS, write E ; for DIASTEREOMERS, write D . b) If the reaction is REGIOSPECIFIC, write R ; if STEREOSPECIFIC, write S . INTERMEDIATE(S) PRODUCT(S) C H 3 H C H 3 H B r C l 2 C l 2 H 2 O H 2 O H 2 S O 4 1 . B H 3 2 . H 2 O 2 , OH - C H 3 O H H 2 S O 4 N a m e : CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 + Diastereomers, Regiospecific Stereoselective Cl Cl HO OH CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 H 2 B H CH 3 CH 3 Cl CH 3 CH 3 Cl + CH 3 CH 3 Cl CH 3 CH 3 Cl + Br + CH 3 Br Diastereomers, Regiospecific CH 3 CH 3 CH 3 HO + CH 3 HO Diastereomers, Regiospecific CH 3 CH 3 CH 3 H 3 CO + H 3 C OCH 3 Diastereomers, Regiospecific (R)-1,5- dimethyl- cyclopentene CH 3 CH 3 CH 3 CH 3 + Diastereomers, Regiospecific Stereoselective HO HO CH 3 CH 3 CH 3 + CH 3 Diastereomers, Regiospecific Stereoselective Cl Cl Cl Cl
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2. MECHANISM (similar to # 57, 58, 59, 67) Propose a mechanism to explain the formation of the products of the following reactions. a) OH H 2 SO 4 O Answer: OH HOH 2 OH
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Unformatted text preview: + H 2 O O H H 2 O 1 3 5 5 1 O b) Give the mechanism for the following reaction. (similar to #57, 58) CH 3 CH = CH 2 + H 2 O H 2 SO 4 CH 3 HO CH 3 Answer: H OH 2 1 3 5 H 3 C H 3 C CH 3 H 3 C CH 3 6 6 1 5 H 2 O H 3 C CH 3 O H H H 2 O H 3 C CH 3 HO 3. SYNTHESIS (similar to #33,63,64) Given the starting materials on the left, provide the following synthesis. CH 3 Br NaOCH 3 CH 3 H 2 SO 4 CH 3 OH H 3 C OCH 3 a) OH CH 3 CH 3 1. BH 3 2. H 2 O 2 , HO CH 3 CH 3 H 3 CO b) Br Δ (Ε2) 1. NaOCH 3 , 2. CH OH, H SO 3 2 4 Cl 2 H2O OH Cl NaH O C CH Na OH C CH 4. ALKYNES - Introduction (#12, 13) Give products for the following reactions. c) 1. C OH C = CH l 2 , H 2 O 2. NaH 3. Na C CH a) CH 3- C C - CH 3 Cl 2 excess b) Cl Cl 1. NaH 2. CH 3 Br CH 3- C C - H H 3 C C C CH 3 Cl C l H 3 C C C CH 3...
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KEY_QUIZ+2-2++51B+W++08 - H 2 O O H H 2 O 1 3 5 5 1 O b...

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