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Magazine Chapter 18: Q66P (page 971)
Solving the following road-map problem depends on determining the structure of A, the key intermediate. Give structures for compounds A through K.
Short Answer
Step by step solution
Determining the structure of A, the key intermediate
The identity of A is hept-2-one.
Structure of compounds from A through K
(a) hept-2-one reacts with phenylmagnesiumbromide and H3O+ forms 2-hydroxy-2phenylheptane.
hept-2-one 2-hydroxy-2phenylheptane
(b) hept-2-one reacts with a Grignard reagent and H3O+ to form another product as 3-(1-hydroxy-1'methylhexyl)cylcohexanone.
hept-2-one 3-(1-hydroxy-1'methylhexyl)cylcohexanone
(c) hept-2-one reacts with HCN to form 2-hydroxy-2-methylhetanenitirile which undergoes hydrolysis to give 2-hydroxy-2-methylhetanoicacid.
(d) pentylmagensiumbromide on treatment with ethanal and H3O+ forms 2-hydroxyheptane which on further treatment with NaOCL/HOAc undergoes oxidation to give hept-2-one.
(e) hexanoic on treatment with SOCl2 to form hexanoyl which further reacts with Gilman reagent to give hept-2-one.
(f) Hydration of hept-1-yne takes place in presence of catalyst HgSO4 , H2 SO4 / H2O to hept-2-one.
(g) 2-methyl-heptan-1-ene undergoes ozonolysis which converts the alkene into carbonyl compound ( hept-2-one).
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