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draw the deprotonated form of benzoic acid, which has the formula c6h5co−2.

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Robert Kubara
Robert KubaraLv10
15 Mar 2021

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Related questions

Which of the following is a weakBrønsted

base?

(a) H3PO4

(b) CH3CH2CO2

-K+

(c) CH3O-K+

(d) (C6H5CO)2O

(e) BF3

A mixture composed of 3-chlorobenzoic acid and acetanilide is added to a seperatory funnel. Diethyl ether is added, and then aqueous sodium bicarbonate solution.

What happens?

Question 3 options:
A)

Acetanilide is protonated and ends up in the aqueous phase.
B)

3-chlorobenzoic acid is deprotonated and is transferred to the aqueous phase.
C)

Benzoic acid is protonated and is transferred to the aqueous phase.
D)

Acetanilide is deprotonated and ends up in the aqueous phase.
Question 3 options:
A)

Acetanilide is protonated and ends up in the aqueous phase.
B)

3-chlorobenzoic acid is deprotonated and is transferred to the aqueous phase.
C)

Benzoic acid is protonated and is transferred to the aqueous phase.
D)

Acetanilide is deprotonated and ends up in the aqueous phase.

1. Here's an interesting paradox. Take a solution of benzoic acidin ether, and add an equal volume of
water. The partition coefficient is about 100, i.e., benzoic acidis 100 times more soluble in ether than in
water. So only about 1% of the benzoic acid goes into the water.Now use aqueous NaOH or aqueous
NaHCO3 instead of plain water. The benzoic acid gets deprotonated,and it all goes into the aqueous
layer. Why doesn't only the 1% that partitions into the water getdeprotonated? It's not deprotonated in
the organic layer, so shouldn't the large partition coefficientkeep most of it in the ether? Something must
be wrong with this reasoning --- what is it?

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