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Chapter 2: 2.17 (page 72)

Which hydrogen in pseudoephedrine, the nasal decongestant in the commercial medication Sudafed, is most acidic?

Short Answer

Expert verified

In pseudoephedrine, the hydrogen atom bonded to oxygen is the most acidic.

Step by step solution

01

Acidic hydrogen

The hydrogen (H) atom that is easily dissociated from a compound/molecule is termed acidic hydrogen.

02

Acidic Strength

The acidity of a hydrogen atom depends on the ‘electronegativity’ of the atom to which it is bonded.

The higher is the atom's electronegativity, the more acidic is the hydrogen attached to it. The electronegative atom pulls the electron density towards itself, leading to the generation of H+ions.

03

Acidity of hydrogen atoms in pseudoephedrine

The structure of pseudoephedrine is shown below.

The most acidic hydrogen in pseudoephedrine

Pseudoephedrine consists of hydrogen atoms bonded to carbon, oxygen, and nitrogen.

Of these, oxygen is the most electronegative. Hence, the hydrogen atom bonded to it is the most acidic.

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Most popular questions from this chapter

Amino acids such as glycine are the building blocks of large molecules called proteins that give structure to muscle, tendon, hair, and nails.

a. Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion.

b. What product is formed when glycine is treated with concentrated HCl?

c. What product is formed when glycine is treated with NaOH?

Acetonitrile (CH3CN) has a pKaof 25, making it more acidic than many other compounds having only C-H bonds. Draw Lewis structures for acetonitrile and its conjugate base. Use resonance structures to account for the acidity of acetonitrile.

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.

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?

Decide which compound is the acid and which is the base, and draw the products of each proton transfer reaction.

(a)

(b)

(c)

(d)
See all solutions

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