compound A has a strong, broad IR absorption at 3200-3500 cm-¹ and the proton NMR spectrum shown. Treatment of Ompound A with H₂SO4 gives compound B, which has the NMR spectrum shown and a molecular ion at m/z = 84 in its EI hass spectrum. Identify compounds A and B. 400 2100 1800 compound A 1500 chemical snitt, MZ 1200 900 600 300 8966 0 2400 2100 1800 compound B 7.1 Hz 1500 chemical shift, Hz 1200 900 74 Hz 600 3842 3774 300 3937 7.6 Hz 0

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Organic Chemistry
Loudon | Parise SEVENTH EDITION
presented by Macmillan Learning
A compound A has a strong, broad IR absorption at 3200-3500 cm¹ and the proton NMR spectrum shown. Treatment of
compound A with H₂SO4 gives compound B, which has the NMR spectrum shown and a molecular ion at m/z = 84 in its EI
mass spectrum. Identify compounds A and B.
2400
8
2100
1800
compound A
1500
6
▬▬▬▬▬▬▬▬▬▬LL LLE THE
7
5
chemical sNITT, MZ
1200
900
Draw compound A.
m/
disappears after
D₂O shake,
600
Mamm
4
3
chemical shift, ppm (8)
1595
L
LLLL LLL
2
300
8966
6165
4461
1
0
0
2400
L
2100
8
1800
compound B
7.1 Hz
▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬
7
ма
6
1500
1346
5
Draw compound B.
chemical shift, Hz
1200
900
T
7.4 Hz
-
with
4
3
chemical shift, ppm (8)
600
3842
3774
2568
2
300
3937
1
7.6 Hz
0
0
Transcribed Image Text:Organic Chemistry Loudon | Parise SEVENTH EDITION presented by Macmillan Learning A compound A has a strong, broad IR absorption at 3200-3500 cm¹ and the proton NMR spectrum shown. Treatment of compound A with H₂SO4 gives compound B, which has the NMR spectrum shown and a molecular ion at m/z = 84 in its EI mass spectrum. Identify compounds A and B. 2400 8 2100 1800 compound A 1500 6 ▬▬▬▬▬▬▬▬▬▬LL LLE THE 7 5 chemical sNITT, MZ 1200 900 Draw compound A. m/ disappears after D₂O shake, 600 Mamm 4 3 chemical shift, ppm (8) 1595 L LLLL LLL 2 300 8966 6165 4461 1 0 0 2400 L 2100 8 1800 compound B 7.1 Hz ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 7 ма 6 1500 1346 5 Draw compound B. chemical shift, Hz 1200 900 T 7.4 Hz - with 4 3 chemical shift, ppm (8) 600 3842 3774 2568 2 300 3937 1 7.6 Hz 0 0
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