Exam1.2002

Exam1.2002 - Chemistry 212 Name Examination 1 I 1[20 Provide the structural formula for the major product of each reaction Clearly indicate any

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chemistry 212 Name Examination 1 I February 13, 2002 1. [20] Provide the structural formula for the major product of each reaction. Clearly indicate any relevant stereochernistry. O H (>20 ‘HZNCNHNHZ / acidic buffer OLOH conc. H2504 A $0 CH30' Na+ in CH3OH 1) triphenyl phosphine 2) n—butyl lithium 3) 3-pentanone 1-bromopropane ——-——————> .2. [20] Provide an appropriate starting compound for each of the following reactions: /_\ O excess HOCHZCHZOH, trace HCl MO ————-——————-—-——> H . yridinium chlorochromate H p (PCC) in CH2C12 1) Mg in anhydrous ether OH 2) 2-butanone 3) H30+ m—chloroperbenzoic acid in CH2C12 ———————————> 3. [20] (a) Provide a detailed, step-by—step mechanism for the following reaction. N—CI—I3 ' O / (j + CH3NH2 ———-——>HC1(aq)’pH:5'8 O (b) The reaction proceeds efficiently at pH = 5.8, but when the reaction is attempted using a solution with pH = 1.2 the reaction does not occur at a measurable rate. Explain this observation. 4. [20] When Compound A (C9H18) is treated with ozone (03) followed by zinc in acetic acid, Compound B (C4H80) and Compound C (C 5H100) are produced in equal quantities. Compound B reacts With 2,4—dinitrophenylhydrazine to produce a yellow precipitate, and it reacts with iodine in aqueous KOH to produce iodoform (CHI3). The H—NMR spectrum for B is given below. Compound C, Which exhibits a strong IR absorption at 1727 cm‘l, reacts with chromic acid to produce a green precipitate and pentanoic acid. WhenC reacts With dimethylamine at pH = 5.8, compound D (C7H15N) is produced. Provide structures for Compounds A, B, C, & D. H—NMR for Compound B. ' 3 2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.5 1.4 1.2 1.0 0.8 0.5 PPM Proton NMR . 21.4 30.2 integral values 31-7 $H3 (IIHs 00—? CH3 Lot—Hi) OOH I—CII—CH3 CH3 CH3 (b) No iodobenzene is produced in_the reaction. Explain this result. ...
View Full Document

This note was uploaded on 04/20/2008 for the course CHM 212 taught by Professor Thomsen during the Spring '08 term at F & M.

Page1 / 4

Exam1.2002 - Chemistry 212 Name Examination 1 I 1[20 Provide the structural formula for the major product of each reaction Clearly indicate any

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online