
Interpretation:
Given that spectroscopic analysis of compound A with formula C5H10O yields the following data:
IR: 3400cm-1; 1640 cm-1
1HNMR: 1.63 δ (3H, singlet); 1.70 δ (3H, singlet); 3.83 δ (1H, broad singlet); 4.15 δ (2H, doublet, J =7Hz); 5.70 δ (1H,triplet, J=7Hz).
i) How many double bonds and/or rings are there in A has is to be stated. ii) The identity of the oxygen containing
Concept introduction:
In IR the O-H stretching of alcohols and phenols are observed in the range 3200-3550 cm-1. The C=C stretching is observed in the range 1620-1680 cm-1. In 1HNMR spectrum, the alcoholic proton absorption occurs in the range 3.4 δ - 4.5 δ while that of phenolic proton occur in the range 3.0 to 8.0. The
The absorption due to 10 alkyl group (CH3) is seen around 0.7 δ - 1.3 δ, that due to a 20 alkyl group (CH2) is seen around 1.2 δ - 1.6 δ while that due to 30 alkyl group (CH) is seen around 1.4 δ - 1.8 δ The multiplicity of a signal gives an idea about the protons present in the adjacent carbons.
To state:
The number of the double bonds and/or rings in the compound A.
To identity:
The oxygen containing functional group from IR spectral data and the protons responsible for the NMR data listed.
To propose:
A structure for the compound A.

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Chapter 17 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
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