EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Chapter 10.1, Problem 7ATS
Interpretation Introduction
Interpretation:
Compound 2 (in question), which has strong antimalarial activity, can be created synthetically from the naturally occurring compound (S)-limonene (compound 1) using radical chemistry. The weakest C-H bond in (S)-limonene needs to be explained.
Concept Introduction :
A substance called limonene is present in various plants and the peels of citrus fruits. Medicine is made with it.
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Give reasons for the following :(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.(ii) (±) 2-Butanol is optically inactive.(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.
An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3).
Draw the structures of A, B, and C. Give the reactions.
Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
Chapter 10 Solutions
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