midterm1-2010answers

Midterm1-2010answers - LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY MIDTERM EXAMINATION I — version 1 CHEMISTRY

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Unformatted text preview: / LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY MIDTERM EXAMINATION I — version 1 CHEMISTRY 302 EXAMINER: Prof. H. Sleiman Monday, February 15, 2010 ASSOCIATE EXAMINER: Prof. B. Arndtsen 6:308:00 pm i. Fill in your name and student number on the exam provided. There is no separate answer sheet for the multiple choice questions. Please circle the correct answer on the midterm paper itself. 2. This exam comprises 9 pages in total (excluding the periodic table page) 3. A periodic table is on the back ofyour exam sheet. 4. Please do not ask Questions to the invigilators about interpretation ofthe exam Questions. If you have a query ofsignificancc. please summarize it on the Front ofthe exam and it will be evaluated. Page 1 Name: Date: 1. What is the final product? Phenol Fbulfiyllglhluridc CIOHHO iZNaOH 7 I 3 (parwisomer) ll.C1‘[3CH2l C? l-fl-Butyl-4-ethoxybenzene ) l-te_rt-But)l-4-ethylbenzene C) l-fl-ButoxyA4-ethoxyhenzene D) m-Butyl ethyl ether E) l-fl-Butoxydethylbenzene 2. When sodium phenoxide is heated to 125°C with carbon dioxide under pressure and the product mixture acidified, which ofthese is produced? 0 OJLOH OH O 0 © 65*)“ “°©*°H I 11 Ill 0 OH 0 OH do“ HO IV V A l [I III D) [V E)V 3. What would be the major product of the following reaction? HOO Br: (excess) 0 ___, H10 ' Br Br H00 H00 HOUBr HOD Br Br Br I l] 11! [V A) 1 B) 11 ‘ - III IV ) A mixture ofl and H Page 2 [I]. (36 marks) Show the products ofthe following reactions: 1. (Give the structurcsqu and B) OH OCHa 1‘ NaOH Heat (200°C) ———————> A —* B . ‘ #5“ OR 2. CH1=CH-CHZBr (\D & \ 0c ' Aqw‘s 0“ a”)? E ; (7,( H30 on \ Brl, FeBr; 5 \7’ \ @ 2. I \ k .4 \ N 015 H H30 \ H G) .4 c1 SJLIHMNA G) I; Lona/1 SUI/AWWHC’" 3' #qfif© CsHa Page 6 4. Which 0fthe following would be the strongest acid? “‘0 Q “’0 CH3 0H 1 [I Ill v 00" 0°” F3C Br _ iv v A) 1 B) 11 III IV E) v 5. Pyrrole is not particularly basic, because the lone pair on the nitrogen is 3 W Eflglfi’fl‘ - 6. What are the products of the reaction of phenol with propanaic anhydride (CH3CH2C(O)OC(O)CH2CH3) in the presence of base? 0—0 0" Q” @ @023A CH3CH2c0; CHgCchoz' CHacHzcoz’ CH3CH2002‘ CH3CHZCHZOH [v V A) 1 )_ II . @111 * . IV E) v Page 3 7. Identify the commercial preparation(s) of phenol, A) Chlorobenzene + NaOll aL 350°C; then H30l B) Benzene + 02 C) C5H5CH(CH3)2 + ()2; then H102 heal D) A) and B) @A) and C) 8. Which of these is an aromatic molecule? CH3 CH3 '1' 6 1 11 E11 IV v I = II C) [II D) IV E) v Page 4 lb [1. (imarks) For each ofthe following pairs of molecules. answer the specific question, and EXPLAIN the a trend. 3. Which of the two molecules is more acidic? Explain briefly with resonance structures (no need to draw all ofthem,ju511he structures that explain the acidity trend) . 0H (9 OH 0? C9 ¢Nm 7 /©\ i2 fi‘m a “I’LLV‘: m» zmd o N L I, ’r DZN No2 7’ no2 Q Cheeng 0-11 “9"me a» mum kald,€\~&m he“ 15H?) (9 C9 Char}, ml- an Chianti“; , 05> ‘40}, (“51, )fi \. k lLII/ e, l / “130.th Clio/Pu. an: an 971/ M W local-,3 NOL ;) “ltd-\mrtlfiln‘ilieal ifllmi 01x50" :3 “VW W :3 (+5 “fluff”, “:4 .1 AW b. Rank the following molecules in their reactivity towards bromine. EXPLAIN using resonance aCfll structures if needed. 0 Q U (933:: @T @O @S H O 7 .40; (Wag > C3) ®E® ‘ l l» sulfur a; was e'rs'éf mCArBDCdfion @E <T><E Orbital ad “Mm 3: rSmDrc amend B H \ H a M‘. ; Mgkc‘ in It 5 G9 0/0 L5 PLAERKKLE m:’h’\ Pages ® befiv‘ c—S 6 H) ‘u N _ v i / 0‘) M'CKGI —5 2. C‘WCI cw “130* . @ t¥ amt] 6w m A:— ® (L V'fnj‘ CEKFLLMK OH OK 0 1, momma; 2:6” a U CH3 2. H30* 55 (E43 0+5 CH3 ' ' Page7 q wwwbm.‘ IV. (12 marks) Show a mechanism for the following transformation . Don’t forget to show the resonance structures far the intermediates. ‘ OH OH H + +‘ HN —> L H H \ ‘3sz CH3 CH3 H @ ("OI H6 ‘C- H “kc/ G H# cm 1—; H‘ ‘ u \ 7 INCL“? (“£3 < K W CLtJ\/Lf\_\’ W 69 ‘ NC L; R :1 _,_n [L/ l ®\ an; < x . 5% H OH H fluf— (a910— /-* / ¥~ / N w [3, cf“ “2 ® / Page X ,1 L V‘ ermarks) Show a synthesis ofth following molecule from the indicated staning material and any needed reagents: N02 CH3 CH \ \ 3 I from l / / N N l) 0103 / Page 9 ...
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This note was uploaded on 03/06/2012 for the course CHEM 302 taught by Professor Sleiman during the Winter '12 term at McGill.

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Midterm1-2010answers - LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY MIDTERM EXAMINATION I — version 1 CHEMISTRY

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