2004exam2 - T‘fAN"" 15 Second Exam 1 Identify the...

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Unformatted text preview: T‘fAN " " 15 Second Exam 1. Identify the compounds (Lewis structure) on the basis of their proton NMR spectral data . given below; (a) CgHm: 1.25(triplet, 3H) 2.6 8 (quartet, 2H) . 7.1 (broad singlet, 5H) - , C (4 L6H 3 I o 5 CH 3 . _ I v s 5 " (b). C5H11Br: 1.18(Sing1et9H) I ‘ j H c —- C " CH 15y 3.3 5 (singlet 2H) 3 I . (c) C6H12 : One Singlet at 2.0 5. + 0H - I JC\ / 3 _ / g C '—"— C N I . / \ _ ~ H} C C/Hj . I I 2. TYAN _ 7 Below are shoWri three C4H3C12 isomers on the left and three sets of H-NMR data on the I right. Match the structures to the proper spectral data (e._g., match (a) with (i) or (ii) or (iii)). (:1 c1 (a) CH3CH2€HCH2 (i) doublet at 5 = 1.5 (6H) and quartet at 6 = 4.1 (2H) C1 C1 . (1,)” ,CH3CHCHCH3 (ii) doublet at 5 = 1.6 (3H), multiplet at- 6 = 2.1 (2H), triplet at 6 = 3.6 (2H) * *jcy a l l (c) CH3CHCH2CH2 (iii) triplet at 6 = 1.0 (3H) multiplet at 8 = 1,9' (2H), doublet at 8 = 3.6 (2H), 'multiplet'atfi _= 3.9»(1H). - How inany signals and of what multiplicity do you expect in the H—NMR spectrum of ‘ CH3CH20CH2CH3? (making? AND M; Qufiflflf L, _ multiplet at 5 _= 4.2 (1H) ' STEVE ' 3‘. . Starting with any moleaules of-your choice But none containing more than fo_ur carbons, .- _ synthesize: ‘ V' s c. s , .. .0» - 3 t . f .. .. OIH 4 ‘ OQC/OH QC/OCH3. _ ‘ (a) A _ “ - . H4". g . .a g ‘2. NO, .' ..M. i I: '3. D“ ‘ ‘ EWQV ‘ \L H. ' HLO . 1" . ‘ .’ ‘ ' ‘.WV%?-.: (b) n-Octane . ..———-) ' - /"\/l .__.—j /\/t H20 I N r n.. u y. In u-.-u- ’6‘ J’Mj)EflaeV . O“ H ‘-. p..p’--'o-vrl ' 0 V V ' i ‘ ‘ LLL PM ' : w' 3 I 20 ' V4. VSTEVE. Starting benzene and ethylene synthesize Ph—CHz—CHfOH. Manse 5.. I Complete the following equations: 0 \ C - OCHZCH3 (a) , ? + ? a Cool-l -. ’ , _ v \C—OCHZCH3 / (b) ? + ? —_————> _ rm _ SOC-“C2, ’ ‘ . I Q ’r 0-“ 3%” l" ‘ 3 3 » mar ‘ COOH . CHZOH ' ‘ . . ? ? I . _ . ———> . _ (c) LIMIA‘ HLO 4 . ‘ 0 . . II ‘ K Cr 0 ' ‘ ' (e) CH3CH2'CH2CH20H '—2—?-—7—> ' ? CH3 CHI—WI 6' \ H 4 . HZSO4 . V 3 0 B . . ~ I Y Ma 3v Mg V . 4 . ‘ . (t) --———> Q ‘ Whatis Q? " ' v Et20 . :7 5 ea _ 0H ,__1 V O . W . A,- ®Q+le m0; ?' [i] 0 . ~ _ V H H+ . - A .(h) 2CH3CH2MgBr + CH3CH2COCH3 ———> -—-—> .? OH 1%} \ OH; 0'42 " C '" o H I \ aqu. MmSE 6. What alg‘ l bromide and what ketone will you combine in the Gfignard synthesis of the» following'alcohols? _ , v . .HO Et- '(CH3CH2)3COH ., OH 0»th . 5 S ...
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2004exam2 - T‘fAN"" 15 Second Exam 1 Identify the...

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