Chemistry Exam: Identifying Products of Organic Reactions, Exams of Organic Chemistry

Download Chemistry Exam: Identifying Products of Organic Reactions and more Exams Organic Chemistry in PDF only on Docsity! I NAN4E: CHEM 3153: Exam 5C I . Which of the fol lowing would be the most l ikely product of the fol lowing reaction? o o il tl /-\r,\-'\ t l v o + l l//-=r' o o il t l /\/\r' t l I I .\a"---_rr--.._- a-"'?o t l \-/ OH 1 . H O - o o o -VocH3 -----[--- ^r-^ocH3 -- AocH3 -focH3 I b) B) I I C) II I A ) I B) I I 6\t \'=-/ 2. HO-, A 1 . N a O C H 3 2. HCI D) rv E),.V 2. Which of the fol lowing would be the most l ikely product of the fol lowing reaction? o z l l- -\.A^^r., v v t t 3 3. Which of the fol lowing would o H o t t l .'^\-r,^\ o o il tl a^\-/\ a\ t l>\r'-\ B) IVI I ITI D) rv E ) V n U 2 l l - r \ . . be the most l ikely product of the fol lowing reaction? NaOH Hzo ,AA, @ " o H D)A ) c) ,AA l4 How can this transformation be accomplished? (Select o ' o 2 he best answer) o 5 . I . Hz, Pd/C II. Hz, Part ial ly Deactivated Pd III. Hz, Lindlar's Catalyst IV. LiAlHq A ) I B) I I 6\vt \-7 How can the following transformation o t l 11 I . CH: I II . CH:MgBr IIL(CHr)zCuLi IV. CHTCHzCHzCHzLt IX. NaOH X. HCI XI. CHgONa XII. LDA, THF XIII. Brz, PBr: XIV. HzO XV. PzOs, A xVI. A A) XVI B) V then XIV C) II then X and XIV D), VI then X and XIV E) III then X and XIV 6. How can this transformation be accomplished? (Select he o t l $ct I. Hz, Pd/C II. Hz, Part ial ly Deactivated Pd III. Hz, Lindlar's Catalyst IV. LiAlHr F) VII G) X then XIII then XIV H) XV then VI then XIV I) IX and XIV then XVI (J t l X and XIV then XVI best answer) -"-'A* V. NaBH+ IX. Na, NH: VI. NaBH+, isopropyl alcohol X. NaOH VII. LiAl lOC(CH:): lrH, -78'C XI. H:O* VI I I . l (CH:)zCHCHzlzAlH,-78"C XI I . HzO E) VI then XII F) VII then XII G ) A o r E fH],B or F \-2 used to accomplish the following transformation? 2 D) Hz, Lindlar's catalyst E) 1. LiAIH+, -78'C; 2. H:O* o A ) I B) II C) II I D) IV then XI 7 . Which of the fol lowing reagents could be % A) CrO:, HzSO+ B) Zn(Hg), HCI C) Hz, Pd/C .'\-'---,,AoH V. NaBH+, CeClr, cold IX. CH:CHzOH W. NaBH+, isopropyl alcohol X. NaOH VII. LiAl lOC(CHr): l :H, *78'C XI. HrO+ VII I . I (CH:)zCHCHzlzAlH,-78 'C XI I . HzO E) IV then XI F) VII then XII G) V and IX and XII be accomplished? ? --------------- > V. NaBH+ VI. LiAIH+ VII. NaBH+, CeCl: VIII. Hz, ft/C 15. Which of the fbl lowing reagents best faci l i tates the reaction shown below? A ) B) c) 16. What alkYl 1 . O : , -78 'C ; 2 'Zn ,HzO 1. Or, -78 'C ' ,2-HzOz l . OsOr : 2 . H :O : bromide should be used in D) KMnO'r' H*, A E) 1. CHTCOTH; 2. H:O* the acetoacetic ester synthesis of the o fol lowing methYl ketone? lr=l,,--u' \/ l-a'' \2 r\-u' \2 7e, IV CH3Br V 19. Which of the fol lowing alcohols A ) I B) II C) III TII D) IV E ) v D) cls-3,4-hexanediol E) trans-3,4-hexanediol is oxidized to a ketone by chromic acid? O H D) IV E ) v I I A)-.t Q)II C) III 17. Which of the following statements describes the first step in the mechanism of the aldol condensation? A)Thea lphahyd rogen isabs t rac tedbyanac id to theeno la tean ion . B) A nucleophile base attacks the carbonyl carbon atom' O-The carbonyl oxygen is protonated by the base ion' f6"lrn^ alpha hydrog"n ir abitracted by the base to form an enolate. t#in;ruonyt o^yg.n of one aldehyde attacks the carbonyl carbon of another' rg. what organic compound is produced when 3-hexyne undergoes ozonolysis fol lowed by hydrolysis? A) propane @iptopunoic acid V:.+-trexanedione rYon (s(\ou \2 \/ (fo* 1,^-4"- (, \-, v I I III TV a 20. Which of the following reagents is not an A) KMnOr B)i Ptg'q'LIf C) CrOr 21. How can this transformation be o --.-A I . Hz, Pd/C II. Hz, RaneY Ni III . Hz, Lindlar's CatalYst IV. LiAIH+ A ) I B ) I I C) III D) IV then XI 12. What is the major organic ' 1 . oxidizing agent? D) PCC E) HIO+ accomPlished? (Select the best product(s) of the following reaction? K M n O a , H O - ' A - 2 2. H3O" V. NaBH+ IX' VI. NaBH+, isoProPYl alcohol X' VII. LiAltOC(CHr):l:H, -78"C Xl VIII. [(CH:)zCHCHz]zAlH'-78'C XII ' answer) OH ,,,,^-----\ Na, NH: NaOH HrO* HzO E) V then XI F) VIII then XI G ) B o r E H ) B o r D o r E l l lv/ o ll r.r ,.,Ar'^*" t l n (J noAvvyo* o I A ) I B) t I C) III 23. What is the major organic A ) I 6 iu 5 r n product of thefol lowing cF3CO3H IN z'-\\ Q'V E; I and IV F) II and III reaction? 2 IV II O ul-3t-tJ3 l l - ,r^.^\ o 9 l l r l ,r\AoH \' eA LJ l l ,^OA IV zJo/ o V II al T> ,z-'--.:-"- III D) IV E ) v a 24. Which of the fol lowing reagents could be used to accomplish the fol lowing transformation? H l \ J t t l -/\-/-" t L/ l i l -\-'\ D) 1. DMSO, (COCI)2, -60"C; 2. EtrN E ) A a n d B F ) A a n d C 25. Which of the following reagents could be used to accomplish the following transformation? o o o H o il ll .,,t\.r-\.,,'\OCH3 t i l -^\-r,,\..'\OCH3 D) L LDA, THF; 2. CH:Br E ) A ( i , ) ' Agzo. NH:: 2. H:o' V pcc, cHzCtz C) O: , -78 'C ? # A) 1. NaBH+; 2. HzO B) l. LiAIH+; 2. HzO C) HCf , Zn(Hg) J