QUIZ+3+KEY -...

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CHEM 5lB PRACTICE QUIZ 3 WINTER’08 M. Taagepera Ch. 11: Alkynes and Ch. 12: Oxidation and Reduction 1. PREDICT PRODUCTS (similar to #35. 36. 37, 40) HCl (1 equiv) Cl 2 1. BH 3 2. H 2 O 2 , - OH H 2 O, H 2 SO 4 , HCl (2 equiv) (1 equiv) 1. NaH 2. CH 3 Br 1. NaNH 2 2. O 3. H 2 O HgSO 4 Cl 2 (2 equiv) Cl Cl Cl Cl Cl Cl H Cl Cl Cl O O OH 4-methyl-2-pentyne 3-methylbutyne 2. MECHANISMS Give the major product and the mechanism for the following reactions or sequences of reactions. a) CH 3 C CH HBr 2 equiv Br Br H Br Br Br Br Br resonance structures Br Br Br H Br 2° carbocation H 3 C
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Give the major product. Show the mechanism for the tautomerization reaction ONLY. b) 1. BH 3 2. H 2 O 2 , - OH OH O tautomerization O OH H O O O O H H OH resonance structures 3. SYNTHESIS (similar to #38, 39, 41, 49, 50, 51, 52, 53, 54, 55) a) Prepare the following compounds from ethyne. State whether the final product is PURE (one stereoisomer) or a MIXTURE of stereoisomers. (1) Br Br Br Br H H H 1. NaNH 2 2. CH 3 CH 2 Br 1. NaNH 2 2. CH 3 CH 2 Br HBr excess (ethyne) pure compound
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Unformatted text preview: -------------------------------------------------------------------------------------------------------------------------- (2) O pure compound H H H O 1. NaNH 2 2. CH 3 CH 2 Br 1. NaNH 2 2. CH 3 CH 2 Br H 2 SO 4 H 2 O HgSO 4 (or hydroboration) (ethyne) b) Prepare the product from the given starting material. CH CH 2 C CCH 2 CHOH CH 3 mixture of stereoisomers (enantiomers) OH Br 2 Br Br NaNH 2 , excess 1) NaNH2 2) O double elimination 1 2 3 1 2 3- epoxide opening occurs from the less hindered side (less substituted) + enantiomer 4. CH. 12 - OXIDATION AND REDUCTION (#32) a) Propose the transition state structure for the following reaction. CH 2 CH 3 CH 3 H 2 Pd-C CH 3 CH 2 CH 3 + CH 3 CH 2 CH 3 H H H 2 Pd/C Pd/C surface b) This is a ____ SYN _______addition and a _____ reduction _______ reaction. (SYN, ANTI) (oxidation, reduction)...
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