Chapter 21: 23P (page 817)
What 1° amine and carbonyl compound are needed to prepare each imine?
a.

b.

Short Answer
a.

b.

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Chapter 21: 23P (page 817)
What 1° amine and carbonyl compound are needed to prepare each imine?
a.

b.

a.

b.

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Use the 1 H NMR and IR data to determine the structure of each compound.

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.

What reagents are needed to convert each compound into butanal?
a.

b.

c.

d.

a. How many stereogenic centers are present in -D-galactose?
b. Label the hemiacetal carbon in -D-galactose.
c. Draw the structure of -D-galactose.
d. Draw the structure of the polyhydroxy aldehyde that cyclizes to - and
-D-galactose.
e. From what you learned in Section 21.16B, what product (s) is (are) formed
when -D-galactose is treated with CH3OH and an acid catalyst?

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