Chapter 19: Q38 (page 758)
Rank the compounds in each group in order of increasing acidity.
a.

b.

Short Answer
a.

Order of acidity: 1>3>2
b.

Order of acidity: 2> 3>1
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Chapter 19: Q38 (page 758)
Rank the compounds in each group in order of increasing acidity.
a.

b.

a.

Order of acidity: 1>3>2
b.

Order of acidity: 2> 3>1
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Question: Identify the lettered compounds in each reaction sequence.
a.
b.
c.
Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.
(a) Explain why the for loss of the first proton () is lower for phthalic acid than isophthalic acid.
(b) Explain why the for loss of the second proton ( ) is higher for phthalic acid than isophthalic acid.

Question: Two other commonly used sulfonic acids are methanesulfonic acid and trifluoromethanesulfonic acid . Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher ?
Glutamic acid is a naturally occurring alpha-amino acid that contains a carboxy group in its R group side chain (Table 19.4). (Glutamic acid is drawn in its neutral form with no charged atoms, a form that does not actually exist at any pH.)

a. What form of glutamic acid exists at ?
b. If the pH is gradually increased, what form of glutamic acid exists after one equivalent of base is added? After two equivalents? After three equivalents?
c. Propose a structure of monosodium glutamate, the common flavor enhancer known as MSG.
Match the values to the appropriate compound. values: 0.28, 1.24, 2.66, 2.86, and 3.12. Compounds: (a) ; (b) ; (c) ; (d) ; (e)
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