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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 鈥榚lectronegativity鈥� 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

Which compound, M or N, is the stronger acid? Explain your choice.

Dimethyl ether (CH3OCH3)and ethanol (CH3CH2OH)are isomers, but CH3OCH3has a role="math" localid="1649252571433" pKaof 40 and CH3CH2OHhas a pKaof 16. Why are these pKavalues so different?

Rank the following ions in the order of increasing basicity:

a.CH3C-H2,CH3O-,CH3N-H

b.CH3-,HO鈥�,Br鈥�

c.

d.

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.

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-.
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