(a)
Interpretation:
The one equivalent of the malonic ester reacted with one equivalent of
Concept introduction:
In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks
In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks
(b)
Interpretation:
The one equivalent of the malonic ester reacted with one equivalent of
Concept introduction:
In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks
In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks
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Chapter 18 Solutions
Organic Chemistry
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- fill the box with the reagents in the correct orderarrow_forwardChoose the best reagents for the following reaction.arrow_forwardThe reaction of a Grignard reagent with a carboxylic acid does not give a secondary alcohol because Grignard reagents only react with aldehydes, ketones, esters, and epoxides. O The carboxylic acid is too sterically hindered to react. The carboxylic acid is not electrophilic enough to react. The Grignard reagent is a base, so an acid-base reaction occurs.arrow_forward
- Use the malonic ester synthesis to prepare each carboxylic acid.arrow_forwardDraw the missing organic structures in this short synthetic sequence. Assume an appropriate workup is performed after each reaction. Convert carbonyls to thioacetals, then treat with Raney Ni/H2 Compound B + Compound Aarrow_forwardWhich would be the best choice of base for a Claissen reaction with propyl acetate? sodium propoxide sodium propanoate sodium ethoxide sodium acetatearrow_forward
- What alkyl halides are needed to prepare each carboxylic acid using the malonic ester synthesis?arrow_forwardDraw the product formed when each organometallic reagent is treated with H2O.arrow_forwardAnswer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.arrow_forward
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