代做CHEM20018 Reactions and Synthesis Tutorial 1代做迭代

CHEM20018 Reactions and Synthesis

Tutorial 1.

1. Draw all the possible enolic (or equivalent) tautomers of the following compounds:

a) 2-pentanone

b) 2,2,6,6-tetramethylcyclohexanone

c) nitromethane

d) methyl butanoate

e) pentanal

2. Although enol tautomers are often present at such low concentrations that they cannot be physically detected using standard methods (e.g infrared or NMR spectroscopy) their presence can be inferred from the chemical behaviour of the carbonyl compound.

In the following two examples enol tautomers are involved in the conversions. Draw mechanisms for the following reactions using just enolisation and its reverse.

3. Explain why optically pure ketone (A) racemizes in basic solution yet (B) does not.

4. Predict the outcome of the following reactions:

Additional Question

AQ1. Compound A (C6H12O) upon treatment with bromine and alkali gives bromoform. and acid B (C5H10O2). Compound B does not react with bromine. Assign structures to A and B.

AQ2. Draw the enolic forms of 1,3,5-cyclohexanetrione. Which tautomer(s) is/are aromatic?

AQ3. Which of the following compounds are enolizable?