Chapter 14: Q.21558-14-61P (page 565)
Propose a structure consistent with each set of data.
a. C9H10O2: IR absorption at 1718cm-1
b. C9H12 : IR absorption at 2850–3150cm-1

Short Answer
Answer
a.

b.

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Chapter 14: Q.21558-14-61P (page 565)
Propose a structure consistent with each set of data.
a. C9H10O2: IR absorption at 1718cm-1
b. C9H12 : IR absorption at 2850–3150cm-1

Answer
a.

b.

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Question. Compound O has a molecular formula C10H12O and shows an IR absorption at 1687 . The 1H -NMR spectrum of O is given below. What is the structure of O?

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.
a.

b.

c.

How many peaks are present in the NMR signal of each labelled proton?
a.

b.

c.

d.

Question: How many 1H NMR signals does each natural product exhibit?
a.

b.

c.

d.

Draw all constitutional isomers of molecular formula C3H6Cl2.
a. How many signals does each isomer exhibit in its 1HNMR spectrum?
b.How many lines does each isomer exhibit in its 13CNMR spectrum?
c. When only the number of signals in both 1Hand 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?
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