PROB. SET #2-1 - CEM 351 Fall 2008 Prof Rathke 2nd Sample...

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CEM 351 Fall 2008 - Prof. Rathke 2nd Sample Problem Set (Chapters 6, 7, 8, 9) 1. Draw the structure of the major organic product (indicate stereochemistry where important) for the reaction of the following alkynes: 1-hexyne, 3-hexyne with each of the following reagents: (in one case, there is no reaction). a) HCl (one equivalent) b) HCl (two equivalents) c) Br 2 (one equivalent) d) Br 2 (two equivalents) e) H 2 (excess), Pd f) H 2 , Pd, BaSO 4 , quinoline g) 1. Li/NH 3 2. H 2 O h) NaNH 2 i) 1) BH 3 2) NaOH,H 2 O 2 j) H 2 O, HgSO 4 , H 2 SO 4 , Δ 2. Outline the steps in an efficient synthesis of the following compounds starting with acetylene: CH 3 CHCH 2 C C H a) b) cis-2-hexene c) trans-2-hexene
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CEM 351 - Dr. Rathke, Fall 2008 – 2nd Sample Problem Set. ... page 2 3. Draw the structure of each of the following compounds: a) b) c) 1-phenyl-1,4-cyclohexadiene 3-methyl-1-butyne acetylene 4. Draw the structure of the major organic product: Li H 2 , Pd CH 3 C CCH 2 show stereochemistry 2 3 (large excess) Cl 2 show stereochemistry . lead acetate, quinoline NH 3
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CEM 351 - Dr. Rathke, Fall 2008 – 2nd Sample Problem Set. ... page 3 5. Draw structures for the intermediate or product of the following reactions: HCl H 2 O H 2 SO 4 , Hg +2 NaOH, H 2 O 2 CH CH CH 3 3 3 BH enol intermediate major organic product 1) 2) major organic product (one equivalent) enol intermediate major organic product (disiamylborane) 2 C C CH 3 3 H 6. CH CHCH 3 CH CHCH 3 CH CH 2 CH 2 . A B C a) Which of the above trienes (A, B, or C) is most stable? b) Which of the above trienes is least stable? c) Which of the above trienes evolves the least heat upon catalytic hydrogenation? 7. Draw appropriate structures in the boxes: + structure of intermediate cation 1,2 product 1,4 product 3 3
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CEM 351 - Dr. Rathke, Fall 2008 – 2nd Sample Problem Set. ... page 4 8. If the following reaction is analyzed after the reaction products have reached a
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This note was uploaded on 10/21/2009 for the course CEM 351 taught by Professor Rathke during the Fall '08 term at Michigan State University.

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PROB. SET #2-1 - CEM 351 Fall 2008 Prof Rathke 2nd Sample...

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