Chem 351 Exam 3 Fall 2000

Chem 351 Exam 3 Fall 2000 - Dr. Hosmane Name: I SS#: CHEM...

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Unformatted text preview: Dr. Hosmane Name: I SS#: CHEM 351 EXAM III December 11, 2000 Q. No. 1: Circle the major product of the following elimination reaction: C 53:45) NaOEt (CH3)ZCHII-v-<:>-w-CH3 —> : EtOH Br‘ (a) (C) (0H3)20H""'<:>'CH3 (D) (CH3)20H—<:>-””CH3 (E) (CH3)ZCHH-~<j>-HIICH3 (F) ((3H3)20H---~<:\>-~--CH3 $2. No. 2: What is the major product of the following reaction? (5 Pb) OH H3PO4 ————~ 6/“ ——> \cu 85 00 CH5 5 9. No. 3: Circle the major product of the following reaction: (5 PB) 0 (1) BHa/THF m..____> O (2) H202/NaOH (A) (B) (C) CH + Enantiomer + Enantlomer Q. No. 4: What is the major product(s) of the following reaction? (51%) CH3CH Br2 H 2w ___+ H/ \CHZCHS CCI4 (A) (38, 4S)—3,4—Dibromohexane (B) (3R, 4R)-3,4-Dibromohexane @(38, 4R)- or (3R, 4S)-3,4-Dibromohexane (D) (38, 4S)— and (SR, 4R)—3,4—Dibromohexane in equal amounts Q. No. 5: Predict the major product(s) of the following reaction: C 5 P45) H30 CH3 (1) Oa/CHZCIZI-78 Oc cu?) CH3 \—/r—\H _> ya + \_.0 H30 (2) ZnIHZO C“ Q. No. 6: Give the correct IUPAC name for the following compound including the stereochemical designation if necessary.: 5 B C 3’ ) CCI3 ®$)_4)535)5_ te'iradwtOY'0... :2, per/i’gne' H30 : CI Q. No. 7: Predict the major product of the following reaction: C 6 916) O HO+ figv©oc O : O —e——» "a Q. No. 8: What is the major product of the following reaction? Show stereochemistry. (a m) __ HZIPd/CaCO3 PR P'le O f“ O “*a' >‘= < H Cf; u Q. N 0. 9: How can this transfonnation be accomplished? C6 PK) OMe H _ H O r; Howome —-——->- H t) Bang/Emu 2) Halo; Cue Q. No. 10: How can the following transformation be accomplished? (6 Pk) ? _ H3C — _——> CH3(CH2)2 CHZPh “3] P4/ l$0504- \ < @0049 :2) mmahloro peflaEMZ—OFC— AQ‘A we?“ $2. No. 11: Starting fiom ethyne, outline the synthesis of (E)-2-hexene, showing each step. You may use any needed reagents and solvents. (mph) . M NU ” (9 + cucucLBr “Cg—CH» HCZCNQ A; N J2; NH +63” uc acaouacuacu3 W 3 chzavfinfliflg P LI/ch- NR3 dual we EC...— CMQUhQ'l-l ._______._7 —--—-—‘> 0% ‘3 .2) Nu4c2 ll “36 H \eu‘lol‘iz 0&3 \PYOJACJt _-_______________4 $2. No. 12: Match the given UV data (taken in heptane as the common solvent) from the left column with the compounds listed in the right column: (10 P“) H C H (A) km 224 nm (a 26,000) (I) 3 — CH3 1 5.11. H O (B) Am 220 nm (a 13,000) + ‘ 311nm (835) l”) HO_©—CH3 I; 111 Hsc _ H CH (c max 243 nm(824,500) () Hac>—$:< 3 H CH3 )9» L—a‘fll (D) Am 236 nm (a 12,600) H3C _ H + (IV) H 314nm (335) H — H H TL (E) Am 214 nm (a 6030) H3C __ H + (V) CH3 273 nm (a 1820) H30 l ; o 31'. $2. No. 13: Which of the following compounds correctly represents the observed mass (6 p46) spectral data? Br 0 H3C\ N / CH3 HO H fl . O N Cl i H (M0 - t. 170) (M01. Wt. 172) (M01. Wt. 172) Observed Mass S ectral Data: m/z 65 (10%), 91 (100%), 170 (12.5%), 171 (0.96%), 172 (12.25%) Q. No. 14: Deduce the compound structure based on its spectral data given below. Identif as many peaks as possible directly on the spectra. ( Io 3N5) o 0 Suggested Structure: /H\/ll\ C MS data: C H O 6103 so do so so 703:- 901wno1ao1aomo1wmm1en1sazm mic "C NMR data: q-13.6; q-24.2; t-59.2; t—46.6; 5—1720; s—207.1 1H NMR data: R ‘2 \ ,6 2 , O ‘ ppm 5 IR data: Wax: Nun-bar. cull 4000 soon 2500 2000 1am 130013001100 moo 900 800 700 9 10 1 I Warwicer microns Q. N o. 15: Deduce the compound structure based on its spectral data given below. Identify as many peaks as possible directly on the spectra. 00 PK) Suggested Structure: MS data: (IBHwOa so 40 so no man m1mnom1w1m1mm1‘n1m1m2m m/e “C NMR data: q-56.0; t-71.0; d-114.3; d-128.3; 5-1609; 5-1332 1H NMR data: llR dala: 1 Wax» Number. on] dmfl Wu 2530 2000 1&0 130013301100 IMO ED am ‘mo i" 5/: fl : Odo ' l—I—‘r' 3 d 5 6 7 B 9 10 11 ‘2 ‘3 14 'IS Wawlorgth. microns ...
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This note was uploaded on 03/04/2008 for the course PSYC 285 taught by Professor Resta during the Fall '08 term at UMBC.

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Chem 351 Exam 3 Fall 2000 - Dr. Hosmane Name: I SS#: CHEM...

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