ACTUAL Exam 2 Practice 140B

5 pts which compound is expected to give the

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Unformatted text preview: 5 pts) Which compound is expected to give the following NMR: O O O O B A D C PART II: Reactions and Synthesis 4. (5 pts each) Provide structures for compounds A thru I. Show stereochemistry where appropriate. H 1) MCPBA 1) THF • BH3 2) NaCN/H2O 2) H2O2/OH- A PCC CH2Cl2 1) PBr3 2) tBuOK NBS CCl4 B HBr I 1) Mg/Et2O 2) H2CO C F NaOEt EtOH heat NaOEt EtOH heat D E G 5. (5 pts each) Provide structures and/or reagents for A thru F. Show stereochemistry where appropriate. 4 O 1) H3C C CNa B A 2) H3O+, heat Cl HBr CN C heat D + CN OCH3 1) E 2) F PART III: Mechanism! 6. (10 pts) Provide a reasonable, detailed mechanism for the following reaction: conc. H2SO4 heat OH 7. (15 pts) Provide a detailed mechanism for the nitration of benzene, showing all steps and intermediates. PART IV: One Last Thing… 8. (15 pts) Starting with 1,3-butadiene, devise a synthesis of 1-phenyl-1,3-butadiene. You may use any other starting materials and/or reagents you wish. Show the major product obtained in each step you propose but do NOT show any mechanisms. You must be clear to receive full (or any) credit. 5...
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This test prep was uploaded on 03/30/2014 for the course CHEM 140B taught by Professor Nefzi during the Winter '06 term at UCSD.

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