Question

Draw the alkyne formed when 1,1-dichloro-3-methylbutane is treated with an excess of a strong base such...

Draw the alkyne formed when 1,1-dichloro-3-methylb

Draw the alkyne formed when 1,1-dichloro-3-methylbutane is treated with an excess of a strong base such as sodium amide. Omit byproducts. (Give the neutralized alkyne product, not the acetylide salt.)

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Concepts and reason

Dehydrohalogenation: Elimination of geminal dihalides to form alkynes

The geminal dihalide is an organic compound which can react with an excess of a strong base such as sodium amide, NaNH,
, will result in the formation of a carbon-carbon triple, bond, followed by water workup produces the final product as an alkyne.

Fundamentals

Dehydrohalogenation Reaction:

excess NaNH,
#
amreang
=
-
H
+
2 Nax
+ NH3
geminal dihalide
alkyne

Mechanism:

| E2
E2
- NaX
- NH3
H
- NaX
- NHÀ
Na NH3
Na NH3
- NH3 Na NH2
Work-up
H

geminal chloride
vinyl chloride
E2
+
NaCl
+
NH3
H
Na NH2

vinyl chloride
E2
う
- NaCl
H
-NH
Na NH3
Na NH2
acid-base reaction
- NHÀ
SONO
acetylide salt
work-up
alkene

Ans:

excess NaNH,

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