Which is the most suitable reagent for the following transformation?

CH3–CH=CH–CH2–CH(OH)–CH3 → CH3–CH=CH–CH2–COOH

Question

Which is the most suitable reagent for the following transformation?

CH3–CH=CH–CH2–CH(OH)–CH3 → CH3–CH=CH–CH2–COOH

Accepted Answer

I2/NaOH. The fragment CH3-CH(OH)- is a methyl carbinol that gives a positive iodoform (haloform) reaction. I2/NaOH cleaves it to a carboxylate (losing CHI3), converting CH3-CH(OH)- into -COOH while leaving the C=C double bond intact. Alkaline KMnO4 would instead cleave the double bond.

Which is the most suitable reagent for the following transformation? CH3–CH=CH–CH2–CH(OH)–CH3 → CH3–CH=CH–CH2–COOH

Solution

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