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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)