classes_fall07_30BID19_Midterm-I-Key

classes_fall07_30BID19_Midterm-I-Key - Manashz...

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Unformatted text preview: Manashz' Charreiy‘ee, 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 --- 1.0 1.7 1.8 1.9 2.1 2.5 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. CH3CH2C1 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 E ' 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? O/K: H2804 (3(4) + H90 —————> ‘ "AK Ho @H (7-) KW G) (g) e ' (7-) L\ H \E: 69 Draws~ the structure of another alkene that can also be formed in the above reaction? l/T\ ( 3) \ Mamashi 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 isopropylamine 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, mod-Pr)4 OH . . 1 (+)—diethyl tartarate —————————> CH2C12, —20°c 1. MsCl, Et3N, CH2C12, trans —4—mefl1ylcyclohexanol ’ 2. HCECNa’THF DJ Mamas/Iii 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 /\/E\ 2‘ Q/OCHS 4- ocH3 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 most 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 QNr «— O” 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. <1) (i) V I l I k‘ 1 x ! R W WW ' Spectrum B is compound 5’ 1 NH bio * rm\ WM i W (W WWW/4 spectrumcrs compound 4* m fr re , \s M W Mi E 1 If i . > ‘E ‘1 U I f ; g Spectrum D is compound z __ 3“": F“ WW mm m N ‘Jt‘ ‘ r ‘f y M» M V i ‘5‘ M SpeetrumEis compound 5 WM ‘ i? i ...
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