Alkynes are less reactive than alkenes towards electrophilic reagents. But the alkyne chemistry is useful for organic synthesis, in the form of hydration of the triple bond, formation of metalacetylides, selective reduction of alkynes and few other related reactions.

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Question: Compare the reactivity of alkynes and alkenes towards electrophilic reagents. Additionally, describe one reaction that demonstrates the utility of alkynes in organic synthesis. Answer: Alkynes, with carbon-carbon triple bonds, are less reactive towards electrophilic reagents compared to alkenes which have carbon-carbon double bonds. This is due to the greater electron density in the triple bond, with two pi (π) bonds. One reaction demonstrating the utility of alkynes in organic synthesis is their hydration, in which a water molecule is added across the triple bond, resulting in an enol that quickly converts to a ketone. This reaction takes place in the presence of a strong mineral acid and HgSO4 as a catalyst.

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1. Understanding Electrophilic Reactivity of Alkynes vs Alkenes

Alkynes, which contain a carbon-carbon triple bond, are less reactive than alkenes, which contain a carbon-carbon double bond, towards electrophilic reagents. The reason for this is due to the greater electron density in the triple bond and the fact that the triple bond is involved in two pi (π) bonds. Alkenes have only one π bond and thus electrophiles can more easily attack and add to the double bond compared to alkynes' triple bond.
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2. Hydration of Alkynes' Triple Bond

Hydration is a reaction in which a water molecule is added across the triple bond of an alkyne, resulting in an enol, which is an alcohol with a double bond. This reaction usually takes place in the presence of a strong mineral acid and HgSO4 as a catalyst. The enol produced is then quickly converted to a ketone through a tautomeric shift for a more stable product.
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3. Formation of Metal Acetylides

Another important reaction in alkyne chemistry is the formation of metal acetylides. This occurs when alkynes react with a metal such as sodium or potassium in liquid ammonia. The metal reacts with the triple bond, inserting itself between the carbon atoms to form a new metal-carbon bond. The resulting compound is called a metal acetylide and can be used as a nucleophile for further synthetic reactions.
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4. Selective Reduction of Alkynes

Selective reduction is a reaction in which only one of the π bonds of an alkyne is reduced to form an alkene. This is achieved by using specific reducing agents that can distinguish between the π bonds. The commonly used reducing agents are sodium in liquid ammonia (trans-selective reduction), or Lindlar's catalyst, which is a poisoned palladium catalyst, and hydrogen gas (cis-selective reduction).
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5. Other Important Reactions of Alkynes

There are also other important reactions involving alkynes, such as the oxidative cleavage of alkynes using ozone (ozonolysis), which leads to the formation of carboxylic acids, and the addition of halogens, which can add two halogen atoms across the triple bond. By analyzing these reactions, we can understand the usefulness of alkynes in organic synthesis despite their lower reactivity towards electrophilic reagents compared to alkenes.

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