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Problems and exercisesCarboxylic acids and derivatives

Exercise 1

What product is obtained by treating methyl hexanoate with (a) LiAlH4, (b) one equivalent of DIBAL-H at −78 °C and (c) excess DIBAL-H at room temperature?

Exercise 2

Propose a synthesis of 1-bromopentane from hexanoic acid, and of octane from hexanoic acid and butanoic acid. What is the drawback of the second?

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