School of Physical & Mathematical SciencesSchool of Physical & Mathematical Sciences Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 7 Spectroscopy, Alcohols, Ethers and Epoxides

1) With the coupling information given, assign the signals due to Ha, Hb and

Hc.

2) Propose a structure consistent with each set of data.

a) C9H10O2 , IR absorption at 1718 cm-1

b) C9H12 , IR absorption at 2850-3150 cm-1

Hc

Hb Ha

CN

Jab = 11.8 HzJbc = 0.9 HzJac = 18 Hz

School of Physical & Mathematical SciencesSchool of Physical & Mathematical Sciences Division of Chemistry & Biological Chemistry

3) A compound with molecular formula C6H10 has a 13C NMR spectrum with 4 lines (δ = 27, 30, 67, 93 ppm). The IR spectrum is shown below. Identify the compound.

4) The following organic compounds are available in your laboratory:

Using the above compounds (not all of them may be useful), and any other organic or inorganic reagents, propose a synthetic route each for the following compounds:

5) Briefly explain the following.

OBrBr OH

OH

OH

HO OHHOOH

OHOH

OH

OH

Cl

base

OH

Cl

base O

no epoxide formation

OOH /H+

O

O

OH

OH

O

(a)

(b)