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Chapter 28: Question 28.51 (page 1149)

What aglycon and monosaccharides are formed when salicin and solanine (Section 28.7C) are each hydrolyzed with aqueous acid?

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01

Salicin and Solanine

Salicin is a type of alcoholic foundin the bark/leaves of willows. Solanine is an alkaloid that originated from the nightshade family plant such as capsicum, tobacco, etc.

Salicin is used for aspirin synthesis if salicin is produced from meadowsweet.

02

Hydrolysis reaction of salicin

When salicin is hydrolyzed with aqueous acid, aglycon and monosaccharides of both anomers are formed.

Hydrolysis reaction of salicin

03

Hydrolysis reaction of solanine

When solanine is hydrolyzed with aqueous acid, aglycon and monosaccharides of both anomers are formed.

Hydrolysis reaction of solanine

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Most popular questions from this chapter

As we have seen in Chapter 28, monosaccharides can be drawn in a variety of ways, and in truth, often a mixture of cyclic compounds is present in a solution. Identify each monosaccharide, including its proper D, L designation, draw in a less-than-typical fashion.

(a.)

(b.)

(c.)

(d.)

A 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and D-talitol. What is the structure of the 2-ketohexose?

For D-arabinose:

  1. Draw its enantiomer.
  2. Draw an epimer at C3.
  3. Draw a diastereomer that is not an epimer.
  4. Draw a constitutional isomer that still contains a carbonyl group.

Classify each compound as identical to A or its enantiomer.

(a.)

(b.)

(c.)

Consider the following six compounds (A-F).

How are the two compounds in each pair related? Choose from enantiomers, epimers, diastereomers but not epimers, constitutional isomers, and identical compounds.

  1. A and B
  2. A and C
  3. B and C
  4. A and D
  5. E and F
See all solutions

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