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Question: a how many chiral centres does the following molecule contain...

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A. How many chiral centres does the following molecule contain? How many stereoisomers are possible? Assign R or S configuration to each stereocentre.

CH3 CH3 OH penicillin

B. Assign E or Z configuration to each of the carbon-carbon double bonds in this chemical structure.

C. Allowing for Markovnikov’s rule draw the product or products from the following reaction. Label major and minor products.

D. Draw the structure of the reaction of the following product with excess bromine. (Show the stereochemistry of the product of the reaction).

E. Propose reaction conditions for transformation of toluene to the products below:

F. An unknown compound W has the molecular formula C8H6 and so clearly has a large degree of unsaturation. When reacted with hydrogen gas in the presence of Lindlar’s catalyst gives a single product X, with the molecular formula C8H8. When X is further reacted with excess bromine the only product, compound Y, has the molecular formula C8H8Br2. When more vigorous conditions are applied to compound Y, including heat and a catalyst, one new compound Z is then formed with the formula C8H7Br3. Draw possible skeletal (line) structures that might represent the products W - Z.

G. Name the compounds drawn below using the IUPAC system of naming (include stereochemical labels if required):

H. Draw the chemical structure for these compounds named using the IUPAC system:

i. 5-(tert-butyl)-6,6-dimethyloct-1-yne

ii. 5-isopropyl-3-propylcyclohept-1-ene

iii. 2,6-di-sec-butyl-4-methylphenol

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