ORGO TEST 2 - {awakens \(ef CHEMISTRY 2020 6.0 SUMMER 2010...

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Unformatted text preview: {awakens \(ef CHEMISTRY 2020 6.0 SUMMER 2010 NAME STUDENT # TERM TEST #2 (2 Hours) Tuesday June 15, 1130-1230 pm Each questions except for (2.19 is worth 5 marks. Q.19 is worth 10 marks Circle the correct answer in multiple choice questions Answer ALL questions on these sheets. DO NOT USE PENCILS FOR FINAL ANSWERS 1. Complete the following reaction by filling in the appropriate reagents. (5 marks) 1 . q _ B\-\3 - 2 . H102. OH I - 'D-eAiuQ’Y 2. muxk5 3% Haoa \s mm\n% 2. Addition of Br2 to (E)-hex-3—ene produces A . (No explanation required) A) a meso dibromide B) a mixture of enantiomeric dibromides which is optically active C) a mixture of enantiomeric dibromides which is optically inactive D) (Z)~3,4-dibromo-3 -hexene E) (E)~3,4-dibrorno—3-hexene (5 marks) 3. Acid catalyzed hydration (H2804/water/A) of an unknown compound (A)with a chemical formula (36le, yielded a racemic mixture of product €5H13OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)? 1 '2 3 A) compound 1 only B) compounds 2 and 3 C) compound 2 only D) compounds 1 and 3 @none of the above / (5 marks) 4. Provide the reagents necessary to complete the following transformation. (5 marks) 3.. Mao/H4” 5. Both ()3)— and (Z)-hex-3 ~ene can be subjected to a hydroboration—oxidation sequence. How are the products from these two reactions related to each other? A The (E)- and (Z)-isomers generate the same products but in differing amounts. he (E)- and (Z)—isomers generate the same products in exactly the same amounts. / ) The products of the two isomers are related regio—isomers. D) The products of the two isomers are related as diastereomers. E) The products of the two isomers are not structurally related. (5 marks) 6. Draw the major organic product generated in the reaction below. Pay particular attention to regio— and stereochemical detail. DH 2. vak 195 OH-rELCR we (5 marks) .lwk‘flvCWSQOK 7. Provide the reagents necessary to carry out the multistep synthesis shown below. I ‘ 0H 8. Provide a detailed, step-by-step mechanism for the reaction shown below. (5 marks) . int-W 9. Predict the structure of the products resulting from the reaction between limonene, a natural terpene found in citrus fruit, and ozone, followed by work up with dimethyl sulfide. “ma .- 4“ 0 Ac. U42, "‘50 sinus " nit ““ ‘9 3“ e 2 (5 marks) c DMS = dimethyl sulphide 39' 3 l i & M55qu CHLO 10. ) In trans-hept—4-en-2-yne the shortest carbon-carbon bond is between carbons 7" WA A landZ Zand3 ‘/ 3and4 D)4and5 E) 6 and 7 (5 marks) 11. To a solution of propyne in diethyl ether, one molar equivalent of CH3 Li was added and the resulting mixture was stirred for 0.5 hour. After this time, an excess of D20 was added. Describe the major organic product(s) of this reaction. H3020) + CH4 ./ B) CH3CECCH3 C) CD3CECD3 D) CH3CECCD3 E) CH30§CD + CH3D (5 marks) 12. Provide the major organic product of the reaction shown below. (5 marks) . _- . . l. NaNHE _ -- _. __ __ 2. PhCHO HacHZC—wCEC-é-ffi? - -~ -IH{? 3. H30 WeCMq.“ we -- °~“-~ en 13. Provide the structure of the major organic product(s) in the reaction below. (5 marks) 14. Provide the major organic product of the reaction below. . . 1.. SiaiBIbTHF (CH3);CHCH3€H3€ECH 2.: H393, H0? (5 marks) 0 WKH 15. Draw (2R, BS) 2-bromopentan—l ,3-diol in a Fischer projection. (5 marks) Maori H B <- H o H 16. What two combinations of Grignard and carbonyl compound can be used to prepare 3-hexanol? Cfisc’t-lz W33“ "‘ 0% /'K H- (5 marks) 1 o D 17. What series of synthetic steps could be used to prepare PhCH(OH)CH2CH3 from PhCI-IZOH? FCC JO Mcfingwksgr (5 m:rks) (h om 0H M3 (9k \ fi,. VWC - H ea; ’3 We‘hmm kamQMn-owe, subsmfi ‘8 MS 1% o-Uulr ox\&n~\iw& 8. When (R)-butan-2-ol ist\r/e'1ted with TsCl in pyridine, the product formed is: a single enantiomer. i a racemic mixture. C) a mixture of diastereomers. D) an achial compound. E) none of the above. 19. What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH? (lOmarks) era- Br” V3546“ ""9 >§ We /A.E>\r\3 er’LO'L OH 9”; o )\/ M N ...
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ORGO TEST 2 - {awakens \(ef CHEMISTRY 2020 6.0 SUMMER 2010...

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