Construct a three-step synthesis of trans-2-pentene from acetylene by dragging the appropriate formulas into the bins....

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Construct a three-step synthesis of trans-2-pentene from acetylene by dragging the appropriate formulas into the bins....

Construct a three-step synthesis of trans-2-pentene from acetylene by dragging the appropriate formulas into the bins. Note that each bin will hold only one item, and not all of the given reagents or structures will be used. (Me = methyl, CH3; Et = ethyl, CH3CH2.)

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Answer 1

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Answer #1

Concepts and reason

This problem is based on the concept of conversion of acetylene to a trans alkene.

Alkynes are highly electronegative due to the presence of triple bonds. They are very reactive towards the chemical species having low electron density. Alkynes can be converted to various compounds with the help of some reaction sequences.

Fundamentals

Reduction of alkynes in presence of lithium or sodium catalyst results in formation of trans alkenes.

The reaction proceeds as follows:

1) NaNH,
2)MeBr
>
HC=
CH
H=
=CH2

The reduction of triple bond proceeds as follows:

1)NaNH,
2)EtBr
CH3 –
HC=
C—
E-
-CH3

Formation of trans alkene proceeds as follows:

1)Li
2)CH,CH,NH,
CH3

Ans:

The correct mechanism is as follows:

1) NaNH,
2)MeBr
1 NaNH,
2)EtBr
> HEC-CH3 —
HCECH
>
—
—
CH3
2CH,CH,NH,
1) Li
2)CH,CHÁNH,

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Answer 2

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