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Chapter 21: 66P (page 817)

Treatment of (HOCH2CH2CH2CH2)2CO with acid forms a product of molecular formula C9H16O2and a molecule of water. Draw the structure of the product and explain howit is formed.

Short Answer

Expert verified

In an acetal, the carbonyl carbon is singly connected to two alkoxy groups. Hemiacetals are generated by combining a carbonyl compound with one alcohol equivalent.

Step by step solution

01

Formation of acetal and hemiacetal

In an acetal, the carbonyl carbon is singly connected to two alkoxy groups. Hemiacetals are generated by combining a carbonyl compound with one alcohol equivalent.

02

Pinacol-pinacolone rearrangement 

The transformation of 1,2-diol into a carbonyl compound happens using the pinacol-pinacolone rearrangement. An acid catalyst is necessary for this reaction to take place.

03

Treatment of  (HOCH2CH2CH2CH2)2CO with acid

The OH group on the right attacks the carbonyl carbon leading to the formation of the hemiacetal. The hemiacetal gets subjected to pinacol-pinacolone rearrangement to form the acetal that can be given as:

Treatment of(HOCH2CH2CH2CH2)2CO with acid

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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.

Draw the products of the following Wittig reactions

a.

b.

Draw the products of each reaction.

a.

b.

Give the structure corresponding to each name:

(a) sec-butyl ethyl ketone

(b) methyl vinyl ketone

(c) p-ethylacetophenone

(d) 3-benzoyl-2-benzylcyclopentanone

(e) 6,6-dimethylcyclohex-2-enone

(f) 3-ethylhex-5-enal

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

a.

b.

c.
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