Question

(10 pts total) Give the structures for compounds/reagents A through K in the following road- map. 6-methylhept-1-yne SOCI2 E (CH3),Culi (1) B (2) H0+ CH),CH(CH)3 MgBr – (1) CH,MgBr in ether (2) H30* Na2Cr2O7 H2SO4 C (1) K (2) H30+ KCN HEN (1) J 4 (2) H30+ H₂O OH &

Answer 1

Grignard reagent on reaction with acetaldehyde 'B' followed by aqueous acidic workup give alcohol 'C' which on oxidation give ketone 'A'. Carboxylic acid 'D' on chlorination followed by reaction with Gilman's reagent give keotne 'A'. hmoor who not macro, H. o A MgBr Na2Cr2O7, H2804 oxidation 2) H30* SOCI (CH3)2Culia A Gilman's reagent H2O, H2SO4 LIAIH4 K 1 5 391 6-methylhept-1-yne 2) H30 Alkynes on hydration reaction give ketones which on reaction with lithiumaluminium hydride give alcohol. PhMgBr J OH 2) H30+ 'A' on reaction phenylmagnesium bromide (Grignard reagent) give alcohol HO CN H30+ I HO CO2H KCN, HCN A on reaction with KCN in presence of HCN give cyanohydrin which on acidic hydrolysis give corresponding carboxylic acid product as shown above.