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Classification of Amines

73 Which is a...

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73 Which is a better nucleophile : Methoxide or tert-butoxide

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Q. (A) Tert butyl methyl ether is not prepared by the reaction of tert butyl bromide with sodium methoxide.
(R) Sodium methoxide is a strong nucleophile.

Q. Assertion :Tert-Butoxide is a stronger base than

O H^{-}

C_{2} H_{5} O^{-}

ion but is a much poorer nucleophile.

B e c a u s e

Reason: A negatively charged ions is always more powerful nucleophile than its conjugate acid.

Q. Assertion :t-butyl methyl ether is not prepared by the reaction of r-butyl bromide with sodium methoxide. Reason: Sodium methoxide is a strong nucleophile.

Q. Consider the dehydrohalogenation of

2

- b r o m o -

- m e t h y l b u t a n e

with ethoxide and

t e r t - b u t o x i d e

. Which of the following statements is true?

When ethyl chloride is added to Sodium tert-butoxide, ethyl tert-butyl ether is obtained as the major product (shown below):

What happens to the rate if the temperature is increased?

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