The chemical shifts of Ha and Hb in the ¹H nmr spectrum of the compound shown below are 0.88 and 3.44 ppm respectively. In comparison the methylene protons in cyclopentane resonate at approximately 1.5 ppm. Explain why Ha and Hb resonate at the given frequencies. Ha. Hb HO. H

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4. The chemical shifts of Ha and Hb in the ¹H nmr spectrum of the compound shown below are
0.88 and 3.44 ppm respectively. In comparison the methylene protons in cyclopentane resonate
at approximately 1.5 ppm.
Explain why Ha and Hb resonate at the given frequencies.
H
H3CH₂CO
5. Using the table provided predict the chemical shifts of the protons labeled a-b in
Compound B below. Show your working.
Ha
Hb
Ha
Ph
Hb HO
dH = 5.25 + Zgem + Z cis + Ztrans
H
Substituent Zgem
0.44
0.98
0.5
1.35
1.00
1.04
1.00
0.23
1.18
1.03
2.09
Alkyl
-C=C
-C=C
Phenyl
CI
Br
COOH
-C=N
-OR
-C(=O)H
OC(=O)R
Zcis
Ztrans
-0.29
-0.21
0.10
-0.10
-0.26
-0.04
0.35
0.37
0.19
0.03
0.40
0.55
1.35
0.74
0.78
0.58
-1.06
-1.28
0.97 1.21
-0.40 -0.67
Transcribed Image Text:4. The chemical shifts of Ha and Hb in the ¹H nmr spectrum of the compound shown below are 0.88 and 3.44 ppm respectively. In comparison the methylene protons in cyclopentane resonate at approximately 1.5 ppm. Explain why Ha and Hb resonate at the given frequencies. H H3CH₂CO 5. Using the table provided predict the chemical shifts of the protons labeled a-b in Compound B below. Show your working. Ha Hb Ha Ph Hb HO dH = 5.25 + Zgem + Z cis + Ztrans H Substituent Zgem 0.44 0.98 0.5 1.35 1.00 1.04 1.00 0.23 1.18 1.03 2.09 Alkyl -C=C -C=C Phenyl CI Br COOH -C=N -OR -C(=O)H OC(=O)R Zcis Ztrans -0.29 -0.21 0.10 -0.10 -0.26 -0.04 0.35 0.37 0.19 0.03 0.40 0.55 1.35 0.74 0.78 0.58 -1.06 -1.28 0.97 1.21 -0.40 -0.67
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