What reagents (s) are needed to do the following 1,2, or 3 step transformations

Question

Question

Answer 1

Answer #1

First reaction,

butanol to butanoic acid

reagent : CrO3, aq.H2SO4 [Jones oxidation]

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Second reaction,

butanoic acid to pentanoic acid [Method 1]

reagents : (a) PBr3 [to from butyl bromide] (b) NaCN [to form pentylnitrile] (c) HCl,H2O,heat [hydrolysis of -CN to -COOH]

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Third reaction,

butanoic acid to pentanoic acid [Method 2]

reagents : (a) PBr3 [to from butyl bromide] (b) Mg,ether [to form grignard reagent (c) CO2 then H3O+ [grignard coupling and acidic workup

-

Fourth reaction,

ethylbenzene to benzoic acid

reagents : (a) KMnO4,KOH [oxidation to form K-salt] (b) H3O+ [acidic workup]

Answer 2

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