(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 17 Solutions
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Propose a mechanism for the Ritter reaction.b. Why does the Ritter reaction not work with primary alcohols?c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols. a. Propose a mechanism for the Ritter reaction. b. Why does the Ritter reaction not work with primary alcohols? c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forwardfill the box with the reagents in the correct orderarrow_forward
- Devise a synthesis of each analgesic compound from phenol (CeH;OH) and any other organic or inorganic reagents. CNH2 ČNH2 CH3 CH3 а. b. C. HO HO CH;CH20 salicylamide acetaminophen p-acetophenetidinarrow_forwardChoose the best reagents for the following reaction.arrow_forwardUse the malonic ester synthesis to prepare each carboxylic acid.arrow_forward
- The 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_forwardWhich would be the best choice of base for a Claissen reaction with propyl acetate? sodium propoxide sodium propanoate sodium ethoxide sodium acetatearrow_forwardWhat alkyl halides are needed to prepare each carboxylic acid using the malonic ester synthesis?arrow_forward
- Draw 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_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_forwardDraw the product formed when each organometallic reagent is treated with H2O.arrow_forward
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