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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

The pKa values of the two ammonium cations drawn below are 8.33 and 11.1. Which pKacorresponds to which cation? Explain your choice.

The C-H bond in acetone, (CH3)2C=O, has a pKaof 19.2. Draw two resonance structures for its conjugate base.

Then, explain why acetone is much more acidic than propane,CH3CH2CH3(pKa=50).

Draw the products of each reaction, and label the nucleophile and electrophile.

a.

b.

Label each statement as True or False.

a.CH3CH2+is the conjugate acid ofCH2=CH2.

b.CH3CH2-is the conjugate base ofCH3CH2+.

c.CH2=CH2is the conjugate base ofCH3CH2-.

d.CH2=CH-is the conjugate base ofCH2=CH2.

e. CH3CH3is the conjugate acid of CH3CH2-.

Compounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes. In which form will amphetamine pass through a cell membrane?
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