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30) (marks5) The molecule shown below is an interesting diterpene (contains 20 connected carbons) derived from phorbol; a natural product isolated from the C. tiglium plant species. Many phorbol derivatives are known to act as tumor promoters and have extensive applications in biomedical research.=

(i) The phorbol derivative above contains many different functional groups. From the list below, identify all the functional groups present in the structure and label each functional group on the structure with the corresponding letter (see example). (a) alkyl group, (b) alkene, (c) alkyne, (d) 1º alkyl halide, (e) 2º alkyl halide, (f) 3º alkyl halide, (g) 1º alcohol, (h) 2º alcohol, (i) 3º alcohol, (j) ether, (k) epoxide, (1) aldehyde, (m) ketone, (n) carboxylic acid, (o) ester, (p) 1º amine, (q) 2º amine, (r) 3º amine, (s) imine, (t) nitrile (ii) How many sp³ hybridized quaternary carbons are present in the phorbol derivative?Circle each on the structure above. (iii) The phorbol derivative contains 4 connected carbocyclic ring systems making up its core structure. Determine the number of carbons contained in each of the 4 carbocycles and label the rings on the structure above as I, II, III, IV respectively.

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