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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

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.

Give the IUPAC name for each aldehyde.

a.2-isobutyl-3-isopropylhexanal

b. trans-3-methylcyclopentanecarbaldehyde

c. 1-methylcyclopropanecarbaldehyde

d. 3,6-diethylnonanal

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–dipole interactions and have comparable molecular weights. Offer an explanation.

Give the IUPAC name for each ketone

a.

b

c

Draw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent

a.

b.
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