Question

Why is α-chloro-2,6-dimethylacetanilide much less basic than 2,6-dimethylaniline?

Why is α-chloro-2,6-dimethylacetanilide much less basic than 2,6-dimethylaniline?

Homework Answers

Answer #1

α-chloro-2,6-dimethylacetanilide is prepared the by the reaction between 2,6-dimethylaniline and α-chloroacetyl chloride.

In 2,6-dimethylaniline, lone pair of electrons is localized on the nitrogen where as in α-chloro-2,6-dimethylacetanilide lone pair is delocalized between the nitrogen and Oxygen through resonance.

Hence α-chloro-2,6-dimethylacetanilide (Presence of Amide group) is less basic than 2,6-dimethylaniline ( Presence of Amine group)

Know the answer?
Your Answer:

Post as a guest

Your Name:

What's your source?

Earn Coins

Coins can be redeemed for fabulous gifts.

Not the answer you're looking for?
Ask your own homework help question
Similar Questions
For The Synthesis of Lidocane answer the following: 1.Why does α-chloro-2,6-dimethylacetanilide only precipitate after an aqueous...
For The Synthesis of Lidocane answer the following: 1.Why does α-chloro-2,6-dimethylacetanilide only precipitate after an aqueous solution of sodium acetate is added? 2.Chloroacetyl chloride is a lachrymator (induces tearing). Give the chemical reaction that occurs on the surface of an eye exposed to this lachrymator. What is the actual agent that produces the irritation and causes the eye to form tears? 3.What happens to the diethylamine that is not extracted from the organic layer when HCl is added and than...
Explain why in order to extract all of the acid form of 2,6-dichloroindophenol out of the...
Explain why in order to extract all of the acid form of 2,6-dichloroindophenol out of the water layer, the solutions must be shaken together.
A project’s PI can be less than 1, but never less than 0. True/False, why?
A project’s PI can be less than 1, but never less than 0. True/False, why?
Why are expenditure multipliers smaller in reality than our basic model predicts?
Why are expenditure multipliers smaller in reality than our basic model predicts?
Last year, East Corporation reported basic and diluted EPS in an amount less than basic EPS...
Last year, East Corporation reported basic and diluted EPS in an amount less than basic EPS due to outstanding stock options. Those options were excercised on January 1 of the current year. During the current year, East Corporation had 15.0 million shares of common stock outstanding. Three thousand eight hundred 10% convertible bonds, each with $1,000 face value, were issued at face amount at the beginning of the year. East reported net income of $3.8 million for the year. Each...
Why on average are women paid less than men?
Why on average are women paid less than men?
Why is a cooling device less efficient than a heat engine?
Why is a cooling device less efficient than a heat engine?
Can a z score be less than 10? (yes or no) and why?
Can a z score be less than 10? (yes or no) and why?
Why are the seasons on Jupiter less intense than on Earth (relatively)?
Why are the seasons on Jupiter less intense than on Earth (relatively)?
Travelers are paying much less for flights to Hawaii in June than they were back in...
Travelers are paying much less for flights to Hawaii in June than they were back in February. Does this represent a shift or a movement​ along​ supply?