F07 midterm1 key

F07 midterm1 key - Manashz' Charreijee, PhD Chem 30 B...

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Unformatted text preview: Manashz' Charreijee, PhD Chem 30 B Midterm I Fall 2007 Student 1]) Number : Name of your TA: Melanie/ Eric /Rob / Chris (Please Circle) Discussion Section — Day : Time: Total: / 100 Chem 30 B Fall 2007 Midterm # 1 (50 mins) Friday October 26 , 2007 - DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO M anashi Charterjee, PhD. Chem 3 0 B Midterm I Fall 2 00 7 1. [16 + 16 points] Give the major product of the following reactions. Please indicate stereochemistry where ever possible. Please indicate “No Reaction” Where appropriate. In the small box indicate S for single product and R for racemic mixture. l.NaH OH ——_+ 2. CH3CHZC1 3. 1. K 06H5 —-———> 2. CH3CH20Ts OH 4. l. KP, lS-crown—6 acetonitrile Mamas/11' Chattelj'ee, PhD, Chem 30 B Midterm I Fall 2007 U1 M24 1' NaOCZHS 1,4 D CZHSOH 6. H304 HI—-"c——OH 7. 9H3 H3CH2C ' OH 1. HCl h» 8. O l Mamas/1i Charteij‘ee, PhD. Chem 30 B Midterm I Fall 2007 2. (15 points) Using curved arrows show detailed mechanism for dehydration of alcohol X to form alkene Y? OH O/K H2804 (aq) + H20 —————> X Hiquszo 1? H36 + H53; (7.) "/N Ho= “\a/H (7‘ ) / /t\ + \J H G) (g) e ' (7-) L\ H \E: 69 Dravs~ the structure of another alkene that can also be formed in the above reaction? l/T\ ( 3) \ Mamashz' Chattezjee, PhD. _ Chem 30 B Midterm I Fall 2007 3. (10 points) Propranolol an antihypertensive agent used in the treatment of high blood pressure can be prepared from l-naphthol, allyl chloride and isopropylamine. Devise a stepwise synthesis of propranolol fiom these starting material. M OApN/K H OH Propranolol ll “ Wm ANHZ l—naphthol allyl chloride isolmjlWla-mine Mamas/1i Chattezjee, PhD. Chem 30 B Midterm I Fall 2 00 7 4. [16 points] Give the major product of the following reactions. Please indicate stereochemistry where ever possible. Please indicate “No Reaction” where appropriate. In the small box indicate S for single product and R for racemic mixture. tert-BuOOH, Ti(O—iPr)4 OH . . 1 (+)—diethyl tartarate —————————> CH2C12, -20°C 1. MsCl, Et3N, CH2C12, zrans—4—mefl1ylcyclohexanol ’ 2. HCECNa’THF DJ Manashi Chattezjee, PhD Chem 30 B Midterm I Phll2007 5. (6 points) How many signals would you expect to see in the 1H NMR spectrum of the following compounds? CH3 1. /©/COCH3 3' H3C CH3 /\/fi\ 2‘ Q/OCHS 4- ooH3 Answer 15 6. (2 points) Which of the following protons (1-5 in structure below) resonate at the highest frequency? (CH3)2CH—O-CH2CH2CH3 Answer 151 —<9\———— 1 2 3 4 5 7. (2 points) Which of the following methyl groups will exhibit the mo st downrield chemical shift in 1H Nl\/£R spectroscopy? 2. CH3OH ———— 3, CH3CH3 5 © 8. (2 points) Which of the following functional groups typically exhibit carbonyl fiequency stretch at the lowest frequency? 1. Amide 2. Ester 3. Ketone 4. Aldehyde 5. Ether Answer is: 2 \l Mamas/11? Charrerjee, PhD. Chem 3 0 B .Midterm I Fall 2007 9. (15 points) A student has carried out the following synthesis but has stored the samples in unlabelled bottles. His research advisor told him to take the IR spectra of the 5 compounds. He obtained a set of 5 IR labeled spectrum A to E. Label the important peaks in the IR and match them to identify the compounds. I 2 l «— 4 (see next page for IR spectra) Mamas/1i Charrerjee, PhD. Chem 30 B Midterm I F all 2007 < P’cs) Spectrum A is compound 52. ) (i) V I l I k‘ 1 x R W ' Spectrum B is compound 5’ 1 NH bio * rm\ Wm i W spectrumcrs compound 4* m fr re , \s M W Mi E If i . > ‘1 U I f ; g Spectrum D is compound z __ 3W”: K“ mm mm m N ‘Jt‘ ‘ r ‘f y M» M i M Spectrum Bis compound 5 WM ...
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F07 midterm1 key - Manashz' Charreijee, PhD Chem 30 B...

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