Courses
Courses for Kids
Free study material
Offline Centres
More
Store Icon
Store
seo-qna
banner

When\[C{H_3}C{H_2}CHC{l_2}\] is treated with $NaN{H_2}$ , the product formed is:
A.168飞艇 b891d240fea97e2e87c8abd11fa16c45
B.168飞艇 7924f1da7caad2ca67287a1ea1a08252
C.168飞艇 173def0956cbe417a47407bcff8c27c9
D.168飞艇 f8cccacddacd411c91c3b1118f398a9e




Answer
VerifiedVerified
302.1k+ views
Hint: To answer this question recall the methods for the preparation of alkyne from dihalides. Sodium amide is a strong reducing agent which removes the halide atoms and generates an alkyne.

Complete Step by step answer:
We know that Sodium amide ($NaN{H_2}$) is a strong base and is used for deprotonation of weak acids and also for elimination reactions. Treatment of either geminal dihalide (two halogens on one carbon) or vicinal dihalides (halogens on adjacent carbons) with two equivalents of $NaN{H_2}$ results in the formation of alkynes.

Understanding the mechanism of this reaction is important: First, there is deprotonation of functional groups which is what is known as initiation of an elimination reaction. In this case, halide atoms are removed to form the alkene. Specifically, this is an example of an E2 (elimination 2) reaction.
Since the alkene still has a halide attached, this too can be removed to generate a second double bond (π bond).
The mechanism of this reaction can be shown as:
168飞艇 57006fa1e093b4b44b9d8f727ca07634
We can see from the above reaction that we receive an alkyne as the major product of the reaction.
Therefore, we can conclude that the correct answer to this question is option B.

Note: We should keep in mind the formation of terminal alkynes by use of this reaction mechanism. The acidity of terminal alkynes plays an important role in major product determination when dihalides undergo base induced elimination reactions. High electronegativity of the triple bond in terminal alkynes makes the molecule acidic. Therefore, one of the base molecules will pull off the terminal hydrogen instead of one of the halides like we desire to happen in this reaction. This implies that we would need three bases for every terminal haloalkane instead of two to obtain an alkyne.