Test_3A - 2 5 Provide the major organic product(s(6 pts...

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Test 2a Chem 2536 – Spring 2004 Name ___________________________ Pledge: I have neither given nor received information from any source while taking this test. _________________________________ 1) For the ketone below, show the acid catalyzed mechanism for the hemiacetal formation. Use arrows in your mechanism denoting movements of electrons. Label the nucleophile and the electrophile. (11 pts) CH 3 -CH 2 -C-CH 2 -CH 3 O H + HOCH 3 2) Circle the most acidic hydrogen on each compound below and rank the compounds from strongest (1) to weakest (3) acid. (9 pts) C-O-H H H H H H H C-O-H O CH 2 -CH-C-CH 2 -CH 3 O H H O O H H O H H H H H CBr 2 C CH 3 O H H ______ ______ ______ 1 Reagents Zn(Hg)/HCl 1)KMnO 4 , - OH 2)H 3 O + MnO 2 NaNO 2 , HCl, 0 ° C H 3 PO 2
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3) Provide the mechanism for the reaction shown below. The first step is provided. Use arrows to show the movement of electrons and use equilibrium reaction arrows where appropriate. (10 pts) N CH 3 C H 3 C H 3 CH 3 CH 3 O 1) CH 3 CH 2 I 2)HOH, H + CH 3 CH 2 -I N + C H 3 CH 3 CH 3 4) Provide the tautomer for each of the given compounds and circle the most stable isomer. (6 pt) CH 3 CCH 3 O CH 3 CH 2 CHCH O CH 2 CH 3 CH 3 CH=C-H OH
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Unformatted text preview: 2 5 ) Provide the major organic product(s). (6 pts each) a. CH 3 CCH 2 COCH 3 O O 1 ) Na +-OCH 3 2 ) CH 3 CHCH 3 Br b. O CH 3 CH 2-NH 2 H + c. CH 3 CH 2 CH N NH 2 Na +-OH ∆ d. O 1)NaBH 4 , 2)H 3 O + e. C H 3 H O excess Br 2 Na +-OH, HOH 3 6) Provide the major organic product(s) of the following reactions. (6 pts each) a. HCCH 2 CH 2 CH 2 CCH 2 CH 3 O O Na +-OH H 2 O C 7 H 10 O b. CH 3 CCHCH 3 CH 3 O P +--CHCCH 3 O 3 A B Na +-CN c. NH O 1)LiAlH 4 , 2)H 3 O + d. CH 2 =CH-CH 2-C-CH 3 O 1 ) 2 ) H 3 O + Li 7) Provide the compound that would yield the following aldol condensation product. CH 3-CH 2-CH-CH-C-C-H O CH 3 H 3 C-H 2 C OH H 3 C Na +-OH HOH 4 8) Provide the methods and reagents to make the following conversions. (5 pt each) a. CH 3-O-C-CH-C-H O O CH 3 H-C-CH-CH 2 O CH 3 b. O C H 3 O C H 3 O O H C H 3 Extra credit (up to 2 pt) Why is De Beers Diamond Trading Company providing labs with free analytical equipment? 5...
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Test_3A - 2 5 Provide the major organic product(s(6 pts...

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