Chapter 21: 68P (page 817)
Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compoundto a furan.
Chapter 21: 68P (page 817)
Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compoundto a furan.
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Get started for freeMaltose 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.
Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).
a. Which carbonyl compound is more stable?
b. Which compound forms the higher percentage of hydrate at equilibrium?
c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?
Explain your reasoning in each part.
What hydrolysis products are formed when the following compound is treated with aqueous acid?
Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan-2-one.
a. Suggest a structure for brevicomin.
b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.
What carbonyl compound and amine are formed by the hydrolysis of each compound?
a.
b.
c.
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