CHM138H-d06-part1 - Name: Student Number: Demo Group:...

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Unformatted text preview: Name: Student Number: Demo Group: UNIVERSITY OF TORONTO FACULTY OF ARTS AND SCIENCE DECEMBER EXAMINATIONS, 2006 CHM 138H1 F Duration: 3 Hours Aids allowed: molecular models. A periodic table is attached to the back of the exam. The examination consists of two parts, I and II. Part I consists of 15 multiple choice questions, worth 2 marks each, which are found on pages 3-7. These questions must be answered on the computer sheet that accompanies this exam. Part 11 consists of 7 short answer questions, worth a total of 90 marks, found on pages 8-11. These questions must be answered on the answer sheets which are attached to the back of the exam. — — — PART I: Multiple Choice Questions. 1. THERE ARE 15 QUESTIONS ON PAGES 3-7. CHECK THAT YOU HAVE THE RIGHT NUMBER OF QUESTIONS AND PAGES. 2. Write your name and demonstrator group number in the box provided on the front of the computer answer sheet. Write your student number in the student ID number field. 3. Using the first m columns only, blacken the circles in the student ID number field which correspond to your student number. Leave the last column blank. YOUR ANSWERS ARE TO BE RECORDED ON THE COMPUTER ANSWER SHEET AND ON THIS PAPER, BOTH OF WHICH MUST BE HANDED IN AT THE END OF THE TEST. NOTHING ELSE WRITTEN ON THE TEST PAPER WILL BE MARKED. DURING THE TEST: 1. Clearly circle on the test paper the letter (A, B, C, D or E) for the b_es_t_ answer you choose for each question. 2. On the computer sheet, blacken the circle (below A, B, C, D or E) which corresponds to the answer you have chosen for each question. Make sure that only one answer is blackened. Make heavy black marks that fill the circle completely. 3. Use soft pencil only (No.2 or softer). DO NOT USE INK OR BALL POINT PEN. 4. Erase cleanly any answer you wish to change. 5. Make no stray marks on the answer sheet. 6. The computer sheet MUST be filled in DURING the time allotted for the test. AT THE END OF THE TEST: Insert your computer answer sheet into your test paper. Remain seated until all test papers have been collected. Page 2 of 19 Part l: Multiple Choice (2 marks each). On the computer sheet, write the letter (A, B, C, D or E) which corresponds to the he_st answer for each of the following questions. 1) Which of the following is the strongest acid? OH OH OH OH OH CHa ~ NO2 Cl 2) Which is the major product of the reaction of 1,2-dimethylcyclohexene with 1) BH3, THF 2) H202, ‘OH ? 0H A? £2?“ £1?“ OH H H A) B) C) w H 5%“ HO OH D) E) 3) Which of the following is the best leaving group in an SN2 reaction? ii ‘ — ' CN- F' CH3O‘ QC H30‘©’fi 0 O A) a) o) D) E) Page 3 of 19 Reactlon Coordinate —o A)1 B)3 C)5 D)4 E)2 5) When 2-bromo-3-methyl-l-phenylbutane is treated with sodium methoxide, why is the major product 3-methyl- 1 -phenyl-1 -butene? A) The newly formed double bond in this compound is conjugated with the phenyl ring. B) The bulkiness of the methoxide ion results in the less substituted alkene. C) An 8N2 mechanism predominates over an E2 mechanism. D) The less substituted alkene is always more stable than the more substituted alkene. E) An E1 mechanism predominates over an E2 mechanism. 6) What is the relationship between the two molecules below? C1 CH3 H3C - H H C1 H OH HO H H OH I H Br Br OH A) They are identical molecules. B) They are enantiomers. C) They are constitutional isomers. D) They are diastereomers. E) They are cis-trans isomers. Page 4 of 19 7) Which of the following species are aromatic? I 0 [CH3 0 @H S H30 CH3 N / . G [‘6 D we 0 Q . CH3 (1) (2) (3) (4) (5) (6) A) 1,5,6 B) 2, 5 only C) 2,4,5 D) 1,2, 3,4,5 E) 2 3 5 8) What is the major organic product of the following reaction? CH3 - OCH3/CH3OH CH3 _____. H30 H30 Br A) (E)-2-isopropyl-1-pentene B) 2,3 -dimethyl- 1 -hexene C) 2,3 -dimethyl-2-hexene -D) (E)-2,3-dimethyl-3-hexene E) (Z)-2,3-dimethyl-3 -hexene 9) The conversion shown below may be 1m described as which of the following types of reaction? A) addition B) substitution C) reduction D) addition and reduction E) substitution and reduction Page 5 of 19 10) The correct reagent or combination of reagents for bringing about the conversion in Question 9 above is: A) 1. CHgMgCl; 2. H30+ D) H2 with Pd/C B) NaBH4/ethanol E) SOClz, pyridine C) PCC in CH2C12 11) Which of the following is an achiral molecule? A) B) C) D) I _ . I \l‘““ '¢ 3 ’1 / ’ / E) ._.||\\\“\ Testosterone is a steroid hormone from the androgen group. It is the principal male sex hormone. It is primarily secreted in the testes of males and ovaries of females. Questions 12 and 13 pertain to testosterone. CH3 OH CH3 l”-~\ I 1 0 ; \\\ I, Testosterone Page 6 of 19 [2) What is the name of the functional group circled in testosterone above? A) carboxylic acid B) aldehyde C) alcohol D) amide 13) none of the above 13) How many chiral centers does testosterone have? A)2 m3 C)4 D)6 ms 14) Which one of the following molecules shows a strong peak in its infrared spectrum at 3500 cm‘1 and no strong peak at 1650 to 1800 cm"? OH HO : i O A) OH O m fig; COO O B) C) D) OCH3 E) 15) Arrange the following molecules in order of increasing rate of reactivity under SNl conditions. Br Br Br A B C D A)D<A<B<C D)A<C<B<D B)D<A<C<B mD<B<A<c -END OF MULTIPLE CHOICE QUESTIONS- C)C<D<A<B Page 7 of 19 PART II: Short Answer Questions. QUESTIONS MUST BE ANSWERED ON THE ANSWER SHEET FOUND AT THE END OF THIS EXAM. Clear and concise answers are essential for full marks. I) (2 marks each). Write the major organic product(s) for the following reactions. Indicate the stereochemistry and regiochemistry where appropriate. CH3 SOCIZ 3) OH —-——> H3C Pyridine ' CH b) 2 FCC H3C OH _——> CHZCIZ H C 3 Br 0) + NaN3 Acetonitrile 0 d ) 1) LiAIH4, ether OH _"—“_+ "" 2) H30 CH3 “ e) 1)03, -78 C ———->+ 2) Zn, H30 CH3 0 Hg(OAC)2’ H20 —-——————> 2) N BH H30 3 4 Page 8 of 19 OH PBr3 Ether Hlo4 H20, THF NaBH4, Ethanol CH3 " " _’ j) 1) NBS, CCI4, hv ——-———-> 2) KOH, ethanol, heat 2) (12 marks). Draw the major products for the two reactions of the molecule shown below. Give the mechanism for each reaction, paying careful attention to regiochemistry and stereochemistry. Use arrows to indicate electron flow. Indicate all intermediates formed, but DO NOT draw structures for transitions states. CH3 . (a) Br X CH3 £I$CHZCH3 CH30', Br ——> Y (b) Page 9 of 19 3) (14 marks). (a) Provide the major product and the mechanism for its formation for the reaction below. Draw the structure(s) of all intermediate(s) but DO NOT draw the structure(s) for the transition state(s). Use arrows to indicate electron flow. (b) Use numbers to label the intermediates in the reaction mechanism you have drawn in 3(a). Draw a free energy diagram and label the location of the reactant, intermediate(s) and the product. How many transition states are there for the reaction below? CH3 Diethyl ether CH3C—CH=CH2 + HCI ———> CH3 4) (12 marks). From the reaction scheme below, draw on the answer sheet the structures of the reactant V, the major organic products W, Y and Z as well as the reagent(s), X. Be sure that the structures that you draw are correct line structures for depicting organic molecules, and that important stereochemistry is shown clearly. H3C _ H3C CH30 X W ——> —-————> + enantiomer \“ H0"‘ Brz, th Cr03/ H3O+/ acetone ether 2) H30+ Y 1) ceHs-Mgarl 2 Page 10 ofl9 5) ( I 2 marks). :1) Draw the product of the reaction for cis-3-hexene with C12. Show the correct stcrcochemistry, but draw only one enantiomer. b) Draw the Newman projection along the C3-C4 bond of the product you have drawn for 5(a). 0) Draw the product you have drawn for 5(a) in Fischer projection. ./=\—_ C|2 —-——-——> H30 CH CH20I2 3 6) (/0 marks). An unknown hydrocarbon A, with formula C6H12, reacts with 1 molar equivalent of H 2 over a palladium catalyst. Hydrocarbon A also reacts with 0504 followed by a workup with NaH803 to give a diol, B. On treatment with ozone followed by reduction with zinc, A gives two fragments. One fragment is propionaldehyde, (‘l l3C| l 2C1 l0 and the other fragment is a ketone C. What are the structures of A, B, and (".’ 7) (/0 marks). How would you carry out the following transformation? More than one step may be required. — END OF THE EXAM — Page 11 of19 6IJ0 2193M i .. m 110021179 :4 I ' 31' :1 g P a at »: 2min M43 ,, ; By a I s 8‘ ’ Rh P8 i *, 'I 'l m ‘ Rn ...
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This note was uploaded on 02/20/2010 for the course CHM CHM138 taught by Professor Andrewdicks during the Spring '09 term at University of Toronto- Toronto.

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CHM138H-d06-part1 - Name: Student Number: Demo Group:...

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