Question

Question: 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

The identity of A is Hept-2-one.

Step-by-step solution

Determining the structure of A, the key intermediate

The identity of A is Hept-2-one.

Structures of compounds from A through K

(a) hept-2-one reacts with phneylmegnesiumbromide and H₃O⁺ forms 2-hydroxy-2-phenylheptane.

(b) hept-2-one reacts with a Grignard reagent and H₃O⁺ to form another product as 3-(1-hydroxy- 1^'-methylhexy)cyclonhexanone.

(c) hept-2-one reacts with HCN to form 2-hydroxy-2-methylheptane nitrile which undergoes hydrolysis to give 2-hydroxy-2-methylheptaneicacid .

hept-2-one 2-hydroxy-3-methylheptane nitrile 2-hydroxy-2-methylhetaneicacid

(d) pentyimagnesiumbromide on treatment with ethanal and H₃O⁺ forms 2-hydroxyhpetane which on further treatment with NaOCI/HOAc undergoes oxidation to give hept-2-one .

(e) hexanoic acide on treatment with SOCI₂ to form hexanoly chloride which further reacts with Gilman reagent to give hept-2-one .

hexanoic acid hexanoly chloride hept-2-one

(f) Hydration of hept-1-yne takes place in presence of catalyst hgSO₄,H₂SO_4,/H₂O to hept-2-one.

(g) 2-methyl-heotan-1-ene undergoes ozonolysis which converts the alkene into carbonyl compound (hept-2-one ).