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Solved: Using the given starting material and any

Chapter 13, Problem 39P

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QUESTION:

Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:

Questions & Answers

QUESTION:

Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:

ANSWER:

Solution 39P

(a)

Synthesis of tetrahydrofuran form but-en-1-ol:

But-en-1-ol reacts with mercuric acetate to form a mercury complex.

The complex formed in the above step undergoes intramolecular  reaction followed by the reduction with sodium borohydride to form a tetrahydrofuran.

(b)

Synthesis of 1-methoxylbutane form but-1-ene:

But-1-ene reacts with HBr in the presence of peroxide to form a 1-bromobutane. This reaction takes place according to Anti Markovnikov’s rule.

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