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Chapter 2: 2.26 (page 78)

Which proton in each of the following drugs is most acidic? THC is the active component in marijuana, and ketoprofen is an anti-inflammatory agent.
a.
b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Acidic hydrogen

The hydrogen atoms linked with any electronegative atoms are more acidic as the electronegative atom drifts the electron density it shares with hydrogen towards itself.

02

Acidic hydrogen in ketoprofen

Acidic hydrogen in ketoprofen indicated in blue

Ketoprofen consists of carbon-hydrogen (C-H) and oxygen-hydrogen (O-H) bonds.

The hydrogen atom bonded to oxygen has higher acidity than the one bonded to carbon as oxygen is more electronegative than carbon.

03

Acidic hydrogen in tetrahydrocannabinol

Acidic hydrogen in THC indicated in blue

Tetrahydrocannabinol consists of carbon-hydrogen (C-H) and oxygen-hydrogen (O-H) bonds.

The hydrogen atom attached to oxygen is more acidic than that attached to the carbon atoms as the electronegativity of oxygen is higher than that of carbon.

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Most popular questions from this chapter

Question: Draw all possible isomers for each molecular formula.

a. $C_{3} H_{7} Cl$ (two isomers)

b. $C_{2} H_{4} O$ (three isomers)

c. $C_{3} H_{9} N$ (four isomers)

What is the $K_{a}$ for each compound?

a.

b.

c.

Bupivacaine (trade name Marcaine) is a quick-acting anesthetic often used during labor and delivery. Which nitrogen atom in bupivacaine is more basic? Explain your reasoning.

Estimate the ${pK}_{a}$ of each of the indicated bonds.

a.

b.

c.

The C-H bond in acetone, ${({CH}_{3})}_{2} C = O$ , has a ${pK}_{a}$ of 19.2. Draw two resonance structures for its conjugate base.

Then, explain why acetone is much more acidic than propane, ${CH}_{3} {CH}_{2} {CH}_{3} ({pK}_{a} = 50)$ .

See all solutions

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