Y10_Test_2_Answers

Y10_Test_2_Answers - NAME SOL-UTIONS RE Z STUDENT#...

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Unformatted text preview: NAME SOL-UTIONS RE Z STUDENT# CHEMISTRY 2020 6.0 FALL TERM 2010 TERM TEST #2 (2 Hours) Thursday December Idmfir ‘3 "H5 m9 SW SECTION A CONSISTS OF MULTIPLE CHOICE QUESTIONS WORTH 20 MARKS IN TOTAL Circle the correct answer in multiple choice questions EACH QUESTION IN SECTION 13 IS WORTH 20 MARKS ATTEMPT FOUR OUT OF FIVE QUESTIONS IN SECTION B Answer ALL questions on these PAGES. DO NOT USE PENCILS FOR FINAL ANSWERS SECTION A MULTIPLE CHOICE. ATTEMPT ALL TEN QUESTIONS IN THIS SECTION 1. Addition of Br2 to (E)-hex-3-ene produces @ a Ineso dibromide a mixture of enantiomeric dibromides which is optically active C) a mixture of enantiomeric dibromides which is optically inactive ”’ D) (Z)-3,4-dibromo-3-hexene // E) (E)-3,4—dibromo-3 -hexene 2. Acid catalyzed hydration (H+/water/HEAT) of an unknown compound (A) with a chemical g formula (361-112, yielded a racemic mixture of product C6H13OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)? 1 I a . '3- A) compound 1 only B) compounds 2 and 3 C) compound 2 only ' /2/ compounds 1 and 3 , @none of the above 3. Which of the following Newman projections does not represent 2-methylhexane? CH3 CH(CH3)2 CH20H3 H H H H H H3C H H CHZCHZCHcha H CH3 H H H H H H CH20H2CH3 CH20H3 CHZCHa CH3 1 2 3 4 A. 1 B. 2 2, D4 4. What is the configuration of the two chiral centers in the following molecule? | | H30 H H30 OH AJRJR 23W flinmw C. 3S,5R D. 38,58 5. When 2,2-dibromobutane is heated at 200°C in the presence of molten KOH, what is the major organic product? A) 1-bromobut—1-yne B) l-bromobut-Z-yne C but— 1 —yne “"3 D but-2-yne (Mm E) but~1~ene 7. In trans-hept—4-en—2-yne the shortest carbon—carbon bond is between carbons 1mm2 2mfl3 C)3mm4 D)4mm5 “v E)6mm7 ah“ 8. Predict the major product of the following reaction. CH3 HEll’ 6.5% .—... 0" o 9. A newly isolated natural product was found to have the molecular formula C15H2802. By hydrogenating a sample of the compound, it was determined to possess one pi bond. How many rings are present in the compound? 65? C) 2 D) 3 - /. E) 4 7 L/ 10. What is the major organic product obtained from the following reaction? - CH3 .Bl'z —-> H20 A. 1 B. 2 17 03 L, @4 SECTION B ATTEMPT FOUR (4) OUT OF FIVE (5) QUESTIONS FROM THIS SECTION EACH QUESTION IS WORTH 20 MARKS 11. Provide the structure of the major organic product of the reactions below indicating stereochemistry where appropriate: (2 marks EACH) 0H (i) “(a 3 H3C H C ' .u H H300“. + 1-3;“. I acetone CHB u k 0/}? 0N8 ",1 rej- "n ‘I max a \ Mk 91‘ % cor (ii) / ‘4 snow 1. 03 i3 ’ ———> ‘4 K 2- ((311923 ”'7 r L, O NaOC(CH3)3 (iv) /- “JR/LOX H ,7 Pi W3 “t "(W w M If] M o H CHS L g \ 9090;: ’1 lequiV- Br: W 4 ——_’ c ‘ M Ufa-CY flab light 306% 35' ogcha (Vi) Br COOH Sou-{92, Zfl/CHS /\ ’7 ' —————-—’— pf, P3 #9 V "aw/Br (vii) w i // 0 ‘C 'fS KL!” 1- SiazBH “fat: \ '7 ‘ w L CH3CHZCH2—CECH —-——> H H M r) 3 2- H202/NaOH M f _‘ -— 7/ (viii) H50 CHI/ i I l. 2 CH3CH2CH2MgBl‘ o H ‘H' OCHch3 2' H30 /\/l\/\ L- CHCI3 % ‘ O 14' / 12(a) Classify the reactions below as an oxidation, a reduction, or neither with respect to the organic substrate. No explanations required. (3 marks) (a) PhCOzH ——> PhCHzOH RWCHDW (b) cis-pent-Z-ene —> pentane R Qéwkcfi'ton fl '\ (c)(CH3)2CHCH20H —> (CH3)2CHCHO o xiW ‘ ‘4 1/ ('11) OH OH 120)) Provide a mechanism for any three of the following: (i) (12 marks) _V / w “m” W - HO 3 4- i H H (iv) Wwegn. 4>/:(. 1' 3H3 —>_/OH 2. H202IOH' fl‘” “1-H \ /' +— J. B\;l'° H L7 fipca 13.(a) 7. Compound A is an optically active alcohol. Treatment of A with chromic acid gives a 5 ketone B. In a separate reaction, A is treated with PBr3 to give a compound C. Compound C is "V then allowed to react with magnesium metal in ether to give a Grignard reagent D. Compound B .1 , \\/V’/ is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product \ E, this solution is found to contain 3,4—dimethyl-3—hex ol. Propose structures for compounds A, B. C.DandE. o2 matva M06» gifMW (10marks) D 4 E. A a C -- " - )' 2 ’ ‘- _ ,. Ix ‘ ” i_/‘ "'L/fl E M L ‘2 omv 3,4 WWW/{4’ W lW\-DJ V; W¢‘;’)W 13(b) Draw both cis and trans—1,4-dimethylcyclohexane in their most stable chair conformations. (4 marks) }\/—m3 a“? 0143 E“ - V): we“ "t 13(0) Which of cis and #ans—dimethylcyclohexane would you expect to have the larger heat of combustion? Explain. ‘ (2 marks) Alf/ram MWWM WAS col/d.“ \ (Lt—>5 W Calm)“ Jug Wiod (Dosiwa hwy-e o M‘ 13(d) Hydrogenation of 1,2-dimethylcyclohexene and 2,3—dimethylcyclohexene both give 1,2- dimethylcyclohexane. 1,2-Dimethylcyclohexene gives only one stereoisomer of 1,2— dimethylcyclohexane, whereas 2,3-dimethyicyclohexene gives a mixture of stereoisomers of 1,2— dimethyl-cyclohexane. Explain. (I “to. m... ‘ 1. 8W5 I 7-“ H102. /O-H' 1" 14(1)) 7 No reaction Brz A (C10H17BT) D (010H1602) 1. LiAIH4 2. H20 E (C10H2002) Br" KOC(CH3)3 (CH3)3COH 1.03 (15 marks) BFZ B (only one product) HglPt 2. (CH3)ZS " C ’?7 % a? 27 H0 72 Z“? E t if X 10 11 15. Prepare the following four Mompounds from the indicated starting materiais. Indicate specific common inorganic and organlc reactants containing NO MORE THAN THREE CARBONS to be used. Each of these synthesis will require at least two steps. (5 marks each for a total of 20 marks) (a) I?“ (‘3) W ' VfM 51; NH": $(5f’pvr‘tlv 79m/ “:1. 3 M\+‘W‘K’OH “II-“M M “"9 W er 8‘ Z woo-A115 g” M 5:3 (c) O M 0—0 ———~ Dec a \L fire/Susk’t‘ T R"C/f“~o—Dl+ 12 M —-~—» /\/\/D W454 er «PM: M L!» ‘r W} fl 7/ or 5% ~ \. M .———-'> ~ ngq 1, amp/0” \ W 2 M‘s gorw’a ...
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This note was uploaded on 06/06/2011 for the course CHEM 2020 taught by Professor Potvin during the Spring '09 term at York University.

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Y10_Test_2_Answers - NAME SOL-UTIONS RE Z STUDENT#...

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