Chapter 7.12, Problem 28P

(a)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.

(b)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.

(c)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.

(d)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.

(e)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.

Hydroboration-oxidation reaction:

• Internal alkynes oxidize to form ketones.
• Terminal alkyne oxidize to form aldehyde.
• Reagents used are ${\text{BH}}_{\text{3}}\text{and}{\text{R}}_{\text{2}}\text{BH}$ for internal alkyne.
• ${\text{R}}_{\text{2}}\text{BH}$ is the reagent used for terminal alkynes.

General mechanism for hydroboration oxidation:

(f)

Interpretation Introduction

Interpretation:

The preparation method for the given compound from acetylene has to be given.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

$Pd/C$: Hydrogenation can done using this catalyst and converts alkenes to alkanes. The addition will be a syn addition.