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Chapter 9: Q9-7P b (page 276)

The pk_aof acetone, CH₃COCH₃, is 19.3. Which of the following bases is strong enough to deprotonate acetone?
(b) $N a^{+}^{-} C \equiv C H$ $({pk}_{a} H_{2} O_{2} of 25)$

Short Answer

Expert verified

Answer:

Yes, strong enough to deprotonate acetone due to more pk_athen acetone.

Step by step solution

01

pka of acetone

pk_ais a number that describes the acidity of the molecule lower the value of pk_astronger will be acidic and easily donate a proton and the higher the value of pk_aweaker will be the acid and stronger will be the conjugate base.

Acetone has a low value of pk_a then $N a^{+}^{-} C \equiv C H$

02

pka of Na+ -C≡CH

pk_aof $N a^{+}^{-} C \equiv C H$ is more than acetone so that $N a^{+}^{-} C \equiv C H$ is the weak acid and the strong conjugate base than acetone due to the strong conjugate base $N a^{+}^{-} C \equiv C H$ able to deprotonate the acetone.

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Most popular questions from this chapter

The oral contraceptive agent Mestranol is synthesized using a carbonyl addition reaction like that shown in Problem 9-50. Draw the structure of the ketone needed.

The final step in the hydration of an alkyne under acidic conditions is the tautomerization of an enol intermediate to give the corresponding ketone. The mechanism involves a protonation followed by a deprotonation.

Show the mechanism for each of the following tautomerizations.

How would you prepare the following carbonyl compounds starting from an alkyne (reddish-brown Br)?

b.

What products would you expect from the following reactions?

b.

Using any alkyne needed, how would you prepare the following alkenes?

(b) cis-3-Heptene

See all solutions

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