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Chapter 17: Q26P (page 823)

What two carbonyl compounds are required for the synthesis of morachalcone A (the aromatase inhibitor discussed in the box below), via a Claisen鈥揝chmidt condensation?

Short Answer

Expert verified

The product followed as:

Step by step solution

01

Claisen-Schmidt condensation

It is also known as cross aldol condensation in which the condensation reaction of aldehyde and carbonyl occurs and the formation of 尾-hydroxyl carbonyl compounds is followed by the nucleophilic attack on enolate ion.

02

Carbonyl compound of morachalcone A

The carbonyl product is condensed to form the morachalcone A and we can identify the two-carbonyl compound from their structure by breaking the double bond two compounds are formed named 2,4 dihydroxy benzaldehyde and 1(2,4-dihydroxy)3-(3-methylbut-2-ene -yl) phenyl) ethenone.

Product formation

03

Synthesis of morachalcone A

  1. The carbonyl compound with alpha carbon reacts with the base leading to the abstraction of the proton.

  2. Carbonyl having no alpha carbon acts as a nucleophile and attacks on enolate of another carbonyl compound.

  3. Followed by loss of water

  4. Formation of the double bond

  5. Condensation product morachaclone A obtained

Formation of morachaclone A

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Most popular questions from this chapter

The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.

Draw the products of the following reactions:

a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

b. pentanoic acid + PBr3 + Br2, followed by hydrolysis

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl

e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + 鈭�

f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl

The ketone whose1H NMR spectrum is shown here was obtained as the product of an acetoacetic ester synthesis. What alkyl halide was used in the synthesis?

Using cyclopentanone as the reactant, show the product of a. acid-catalyzedketo鈥揺nolinterconversion. b. an aldol addition. c. an aldol condensation.

Draw the products of the following reactions:
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