formulate a 4 step synthesis. reagents listed OH 4-STEP SYNTHESIS HO 2 NaNH, NaH

Question

Question

OH 4-STEP SYNTHESIS HO 2 NaNH, NaH

formulate a 4 step synthesis. reagents listed

Answer 1

Answer #1

HO kon OH EN O HEN 2NaNH

Step 1:

Formation of terminal alkyne from the double elimination of dichloro starting material using sodamide base.

Step 2:

Deprotonation of the alkyne proton using sodium hydride base gives the alkynide anion.

Step 3:

S_N2 reaction between the alkynide anion and ethylene oxide gives the alkoxide species.

Step 4:

Protonation of alkoxide with water furnishes the target molecule.

Answer 2

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