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Chapter 21: 33P (page 817)

Safrole is a naturally occurring acetal isolated from sassafras plants. Once used as a common food additive in root beer and other beverages, it is now banned because it is carcinogenic. What compounds are formed when safrole is hydrolysed with aqueous acid?

Short Answer

Expert verified

Cyclic acetal is hydrolyzed using a strong acid to form the corresponding carbonyl compound and diol. The presence of a strong acid would facilitate the formation of the -OH group which is the leaving group in the reaction.

Step by step solution

01

Cyclic Acetal

Cyclic acetal is hydrolyzed using a strong acid to form the corresponding carbonyl compound and diol. The presence of a strong acid would facilitate the formation of the -OH group which is the leaving group in the reaction.

02

Hydrolysis

Hydrolysis of Safrole would give a molecule of formaldehyde and 4-allylbenzene-1,2-diol given as follows,

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Most popular questions from this chapter

Maltose is a carbohydrate present in malt, the liquid obtained from barley and other grains. Although maltose has numerous functional groups, its reactions are explained by the same principles we have already encountered.

a. Label the acetal and hemiacetal carbons.b. What products are formed when maltose is treated with each of the following reagents: [1] ; [2] and HCl; [3] excess NaH, then excess ?c. Draw the products formed when the compound formed in Reaction [3] of part (b) is treated with aqueous acid.The reactions in parts (b) and (c) are used to determine structural features of carbohydrates like maltose. We will learn much more about maltose and similar carbohydrates in Chapter 28.

Devise a synthesis of each compound from cyclohexene and organic alcohols. You may use any other required organic or inorganic reagents

a)

b)

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

The boiling point of butan-2-one ( 79.64oC ) is significantly higher than the boiling point of diethyl ether ( 34.6OC), even though both compounds exhibit dipole鈥揹ipole interactions and have comparable molecular weights. Offer an explanation.

Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis,is used as an additive in cattle feed. Digoxin is a widely prescribedcardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.
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