SampleTEst1A_2204-6-8 Answers1

SampleTEst1A_2204-6-8 Answers1 - and all charges(if...

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Chemistry 2204/6/8 Sample Test 1 Answers Name: Marks are in parentheses 1 (3) For each of the molecules shown below, point out, with an arrow , the carbons bearing the acetal functionality. 2a (6) Draw the corresponding enol tautomer (s) of each ketone/aldehyde in each case. Name the ketone/aldehyde in each case 6 O O enol enol F F H OH F F 1 2 3 4 5 3,3-difluorohexan-2-one 1 2 3 4 5 OH H pent-4-enal 2b (1) Rank the following 3 molecules with respect to oxidation level. (1) highest (3) lowest HO O 3 1 2 3a (8) Show the reagents necessary for each reaction. O H HO CN O O H OH H 2 C O H H 3 CO H O H OH O - CH 2 -P + Ph 3 HCN - CN H+ or -OH ALDOL reaction CH 3 OH H+ 3b (8) Show the starting material which would lead to product. R-C(=O)OOH H+ O O O O 6Cl 2 H + , 1.NaBH 4 2. H + + H 2 O OH Cl Cl Cl Cl Cl Cl O O O O O or OH HO
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Chemistry 2204/6/8 Sample Test 1 Answers Page 2. 3c (8) Show the expected product(s) for each of the following reaction HO HO O H+ O O NH 2 OH H + 1. NaH HO H + O HO + H 2 O diketo tautomer 2. CH 3 CH 2 I O O O HO HO O O O or O O NOH 4a (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement
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Unformatted text preview: and all charges (if applicable). O H NH 3 + H + H 2 O HN H H 3 N H O-H 2 N H OH H + H 2 N H OH H H 2 N H 4b (6) Use the appropriate pKa equations to show why - OH (pKa H 2 O 15.7) cannot be used to quantitatively deprotonate acetone CH 3 C(=O )CH 3 (pKa 20). HOH + H 2 O = -OH + H 3 O + K = 10 -15.7 eqn1 CH 3 C(=O )CH 3 + H 2 O = CH 3 C(=O )CH 2-+ H 3 O + K = 10 -20 eqn 2 Add eqn 2 + reverse of eqn1: -OH + CH 3 C(=O )CH 3 = CH 3 C(=O )CH 2-+ H 2 O K= 10 +15.7 x 10-20 = 10- 4.3 Unfavourable equilibrium constant. . reaction will not proceed to completion 5 (4) Synthesis. Show how aldol reactions can be used to synthesize the following α , β-unsaturated carbonyl-containing compounds. Show the intermediate aldol formed in each case. See next page O O O OH HO O O OH via Aldol intermediate O OH O O...
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SampleTEst1A_2204-6-8 Answers1 - and all charges(if...

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