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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Phantum on November 24, 2021, 05:31:23 AM

Title: Synthesis of isopentyl acetate
Post by: Phantum on November 24, 2021, 05:31:23 AM

Hello, I need help in the synthesis of isopentyl acetate from 1-bromo-2-methylbutane. I am not allowed to use SN1 or E1 reactions. I am only allowed to use SN2 reactions, reactions that involve the use of PBr3, SOCl2, or TsCl, E2 reactions, and any necessary alkene addition reaction. I also cannot use NBS, carboxylic acid added with SOCl2, and a step that produces acid chloride since they are not discussed.

I really don't know where to start but I think maybe the first step will be the conversion of the alkyl halide to alkene via a small base like NaOCH3, then conversion of the alkene to alcohol. Please help me, thanks.

Title: Re: Synthesis of isopentyl acetate
Post by: Babcock_Hall on November 24, 2021, 10:40:54 AM

Why would you use a small base, as opposed to a large base?

Title: Re: Synthesis of isopentyl acetate
Post by: rolnor on November 25, 2021, 11:11:16 PM

How about SN2?

Title: Re: Synthesis of isopentyl acetate
Post by: Babcock_Hall on November 26, 2021, 09:43:05 AM

@OP,
Why would a large base be a better choice here?