exam3b - CHEM 2312 Examination SB Feb . 27, 2009 Name: WWW...

Info iconThis preview shows pages 1–9. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: CHEM 2312 Examination SB Feb . 27, 2009 Name: WWW h I. Multiple choice (circle the right answer, 3 points each) 1. Which of the reagents listed below would efficiently accomplish the transformation of 2—methyl-3-cyclopentenol into 2-methyl- 3-cyclopentenone? OH O WES—“:3 A) H2,Pt B) Bl'2, CCI4 ® CFOa/HzSOA, D) KMnO4(aq, alkaline) E) Two of the above 2. Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH20H2CHO into CH3CH20H=CHCH20H20H20H? A) H2. Ni B) KMnO4 ® NaBH4 D) Br; in CCI4 E) Two of the above 3. What is the major product of the following reaction sequence? HCN H2804 0:0 —> —-> H20 heat CN H I O=N0803H EOH O—cru G—OSOaH 0:0an I II III IV V A) l @ II C) “I D) IV E) v Page i 4. What would be the product of the following reaction sequence? 0H i) P03 9 O 11) CGHG, ' iii) Zn(Hg), HCl, heat 0 O OH W (BMW M I II III IV V A) I B) n C) m D IV v 5. Which of these reduction reactions is unsuccessful? A) T CBH50H2C=O + NaBH4, B) fi CsHsCCHzCHzCH2CH3 + NaBH4, C) if CH3CHZCHZCOCH2CHZCH3 + LiAlH4, ether @ fi CH3(CH2)1OCOH + H2, Pt, pressure E) All of these are successful reductions. Page 2 6. Which compound is an acetal? o (Oj‘OH (oj‘ocm Eoj IOT‘OH I II III IV A)I ® II C) m D) IV E) All ofthe above 7. The Baeyer-Villiger oxidation of propiophenone (ethyl phenyl ketone) produces chiefly: A) (I? CeH5CCHZCH20H B) (i CHgCHZOCCGHs C) R CH3CHZOCOCGH5 D) (d p-HOCsH4CC HZCH3 ® 0 || CaHsocCHZCHa 8. The reaction of lithium di-g—butylcuprate with isopentyl bromide yields: A) 3,5—Dimethylheptane @ 2,5-Dimethylheptane C) 3,6-Dimethylheptane D) 2,6-Dimethylheptane E) 3,4—Dimethylheptane P909 1 9. What is the product, A, that would be obtained from the following reaction sequence? 0 EtMgBr ch'—sz H30* —~ QCECCHZCHa QCECCHZCHQOCHQCHa QCECCHZCHZOH CH3 CHSCHZ CECCH CH OH CECOCIIHCHZCH3 2 2 IV V A) l B u Ill D) IV E) v 10. What is the final product of the following reaction sequence? 0 I CH3] M L. 32%, A H30+ acetone 0 OH m w w I II III A) I B) u C) m D) IV Page 4 11. Which reaction is an oxidation? A) RCH20H -—-> RCHO B) RCHon —> R002H C) RCHO —> RCOzH D) Two of these @ All of these 12. Select the correct reagent(s) for the following reaction: ii ?“ CH3CCHZCHZCOZCH3 ———> CH3CHCHZCHZCOZCH3 A) LiAlH4/ether; then H30+ B) NaBH4; then H30+ C) H2 with Pt/C ® B) and C) E) A), B) and C) 13. Your task is to synthesize 2-phenyl-2-hexanol through a Grignard synthesis. Which pair(s) of compounds listed below would you choose as starting materials? A) ('3) CHgCH2CHzBI‘ and CHacCeH5 B) CHscHCHzBr O | and CH3 CH3CCSH5 ® fi CH30H20H20H200H3 and CGHSBI‘ D) Answers A) or B) E) Answers A) or C) Page 5 14. Which of these compounds will mt be reduced by LiAlH4? A) 0 || CH3CHZCHZCOCH3 ® CH30H20H20H=CH2 C) fi CH3CHZCH200H3 D) 0 II CH3CH20HZCOH E) H CH30H20H20=O 15. Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound? e clm CeH5CHOCH3 B) (i CBH5COCH3 C) CGH5C(OCH3)3 D) Answers A) and B) E) Answers B) and C) l|..Short answer (15 points). What is wrong with the following? 16. o 0 Br Bng Page 6 18. OH HgCrO4 Page 7 OH mob-on W'LL Lu”- L: give throqh't o—u‘A Ill. Short answer (10 points each): 19. Write a mechanism for the following: |-||\/\/\ HO- O OH -——-—> 0/ OH U the) 20. Consider the total oxidation numbers of the bold-faced carbons and indicate whether the reaction is an oxidation, reduction, or neither. 0 o G OH . CA: —i GA. H110 ’% +2 c2» "' C21+3 “*"‘ OMOCQA‘W‘W Page 8 IV. Long Answer (20 points): Suggest a synthesis of the following compound, using reagents with 6 or fewer carbon atoms. (Note, number of carbons doesn’t count if those carbons aren't incorporated in final product). H3C H H O H a db :7 Q + AWL Page 9 ...
View Full Document

This note was uploaded on 09/12/2011 for the course CHEM 2312 taught by Professor Baron during the Fall '07 term at Georgia Tech.

Page1 / 9

exam3b - CHEM 2312 Examination SB Feb . 27, 2009 Name: WWW...

This preview shows document pages 1 - 9. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online