Chapter 20: Q11P. (page 1057)
Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a)
(b)
(c )
(d)
(e)
(f)
Short Answer
(a)

(b)

(c)

(d)

(e)

(f)

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Chapter 20: Q11P. (page 1057)
Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a)
(b)
(c )
(d)
(e)
(f)
(a)

(b)

(c)

(d)

(e)

(f)

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The following NMR spectra correspond to the compound of formula (A) C9H10O2, (B) C4H6O2, C6H10O2 . Propose structure, and show how it is consistent with the observed absorptions.
(a) The isoelectric point (pI) of phenylalanine is pH 5.5. Draw the structure of the major form of phenylalanine at pH values of 1,5.5, and 11.
(b) The isoelectric point of histidine is pH 7.6. Draw the structures of the major forms of histidine at pH values of 1, 4, 7.6, and 11. Explain why the nitrogen in the histidine ring is a weaker base than theα -amino group.
(c) The isoelectric point of glutamic acid is pH 3.2. Draw the structures of the major forms of glutamic acid at pH values of 1, 3.2, 7, and 11. Explain why the side-chain carboxylic acid is a weaker acid than the acid group next to the-carbon atom.
The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.
(a) How many asymmetric carbon atoms are there in an aldotetrose? Draw all the aldotetrose stereoisomers.
(b) How many asymmetric carbon atoms are there in a ketotetrose? Draw all the ketotetrose stereoisomers.
(c) How many asymmetric carbon atoms and stereoisomers are there for an aldohexose? For a ketohexose?
Acetals can serve as protecting groups for 1,2-diols,as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called as acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.
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