The target molecule should be drawn and identified for the given string molecule by using its molecular formula. Concept Introduction : Birch reduction: The conjugated alkynes and benzenes in the presence of sodium metal in liquid ammonia and alkyne produced a non-conjugated diene system. The alkyne involves sodium ( Na ) /NH 3 . Further alkyne triple bond end parts reducing to give the trans ( E ) alkene. Metal reduction: The alkyne molecules can also be reduced to trans alkenes via an entirely different reaction called dissolving metal ( Na/NH 3 ) .

Question

Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

Answer 1

Question

Chapter 9.5, Problem 12CC

Interpretation Introduction

Interpretation:

The target molecule should be drawn and identified for the given string molecule by using its molecular formula.

Concept Introduction:

Birch reduction: The conjugated alkynes and benzenes in the presence of sodium metal in liquid ammonia and alkyne produced a non-conjugated diene system. The alkyne involves sodium (Na)/NH3 . Further alkyne triple bond end parts reducing to give the trans (E) alkene.

Metal reduction: The alkyne molecules can also be reduced to trans alkenes via an entirely different reaction called dissolving metal (Na/NH3) .

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?

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