Vicinal dihalides undergo double dehydrohalogenation to give terminal alkyne. How many moles of\[NaN{H_2}\] are used in the overall reaction?
A.One
B.Two
C.Three
D.Four
Answer
660.9k+ views
Hint: The dehydrohalogenation is the removal of \[HX\] from the molecule where \[H\] is hydrogen atom and \[X\] is halogen atom. \[NaN{H_2}\] acts as a strong base that has the ability to abstract protons.
Complete step by step answer:
The vicinal dihalides undergo dehydrohalogenation to generate terminal alkynes. The reaction goes through a stepwise manner.
In the first step, one mole of \[NaN{H_2}\] abstracts the acidic proton from the dihalide to yield an alkenyl bromide. The protons flanked between the two bromo attached carbons are mildly acidic in nature. Due to the use of \[NaN{H_2}\] which is a very strong base allows the proton to abstract and leads to the alkene intermediate.
In the second step, the alkene intermediate consumes a second-mole \[NaN{H_2}\] to give an alkyne by dehydrohalogenation. The proton abstraction from alkene is easier than in the first step as alkenes are more acidic than alkanes.
Due to the generation of terminal alkynes which are very much acidic in nature the proton from the alkyne gets easily abstracted. But the reaction after aqueous workup yields the desired alkyne compound. From alkane to alkene to alkyne the percentage of s-character increases. As a result the electronegativity increases and the acidic nature increases. Hence alkynes are highly acidic in nature and the third mole of \[NaN{H_2}\] will be consumed during the reaction course.
Thus three moles of \[NaN{H_2}\]are used in the overall reaction.
Note:
The proton on the left side is not abstracted by \[NaN{H_2}\] as it is attached to a carbon that is attached to the methyl group. As methyl groups are electron donating in nature so the acidity of the proton decreases.
Complete step by step answer:
The vicinal dihalides undergo dehydrohalogenation to generate terminal alkynes. The reaction goes through a stepwise manner.
In the first step, one mole of \[NaN{H_2}\] abstracts the acidic proton from the dihalide to yield an alkenyl bromide. The protons flanked between the two bromo attached carbons are mildly acidic in nature. Due to the use of \[NaN{H_2}\] which is a very strong base allows the proton to abstract and leads to the alkene intermediate.
In the second step, the alkene intermediate consumes a second-mole \[NaN{H_2}\] to give an alkyne by dehydrohalogenation. The proton abstraction from alkene is easier than in the first step as alkenes are more acidic than alkanes.
Due to the generation of terminal alkynes which are very much acidic in nature the proton from the alkyne gets easily abstracted. But the reaction after aqueous workup yields the desired alkyne compound. From alkane to alkene to alkyne the percentage of s-character increases. As a result the electronegativity increases and the acidic nature increases. Hence alkynes are highly acidic in nature and the third mole of \[NaN{H_2}\] will be consumed during the reaction course.
Thus three moles of \[NaN{H_2}\]are used in the overall reaction.
Note:
The proton on the left side is not abstracted by \[NaN{H_2}\] as it is attached to a carbon that is attached to the methyl group. As methyl groups are electron donating in nature so the acidity of the proton decreases.
Recently Updated Pages
If x a + bt + ct2 where x is in meters and t is in class 11 physics CBSE

A car covers the first half distance between two places class 11 physics CBSE

The resultant of two vectors overrightarrow P and overrightarrow class 11 physics CBSE

Find the value of cos 135 class 11 maths CBSE

A mass M is held in place by an applied force F and class 11 physics CBSE

A solution of glucose in water is labelled as 10 dfracwv class 11 chemistry CBSE

Trending doubts
One Metric ton is equal to kg A 10000 B 1000 C 100 class 11 physics CBSE

Find the value of the expression given below sin 30circ class 11 maths CBSE

What do you mean by retardation What is its SI uni class 11 physics CBSE

Draw a diagram of nephron and explain its structur class 11 biology CBSE

10 examples of friction in our daily life

Difference between physical and chemical change class 11 chemistry CBSE

