(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
- 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. Why does the Ritter reaction not work with primary alcohols? b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.arrow_forwardA b,g-unsaturated carbonyl compound rearranges to a more stable conjugated a,b-unsaturated compound in the presence of either acid or base. a. Propose a mechanism for the base-catalyzed rearrangement. b. Propose a mechanism for the acid-catalyzed rearrangement.arrow_forwardA B,Y-unsaturated carbonyl compound rearranges to a more stable conjugated a,ß-unsaturated compound in the presence of either acid or base. a. Propose a mechanism for the base-catalyzed rearrangement. b. Propose a mechanism for the acid-catalyzed rearrangement. H30t or HO B.y-unsaturated a,B-unsaturated carbonyl compound carbonyl compoundarrow_forward
- What nitro compound, nitrile, and amide are reduced to each compound?arrow_forward4. Draw the ketone tautomer of each enol present under slightly acidic conditions. -O Harrow_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
- What alkyl halide is needed to prepare each 1° amine by the Gabriel synthesis?arrow_forwardWhich would be the best choice of base for a Claissen reaction with propyl acetate? sodium propoxide sodium propanoate sodium ethoxide sodium acetatearrow_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_forward
- Answer 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 phenylacetic acid (C6H5CH2COOH) is treated with each reagent. With some reagents, no reaction occurs. a. NaHCO3 b. NaOH c. SOCl2 d. NaCl e. NH3(1equiv) f. NH3, ∆ g. CH3OH, H2SO4 h. CH3OH, −OH i. [1] NaOH; [2] CH3COCl j. CH3NH2, DCC k. [1] SOCl2; [2] CH3CH2CH2NH2 (excess) l. [1] SOCl2; [2] (CH3)2; [2] (CHarrow_forwardWhat alkyl halides are needed to prepare each carboxylic acid by the malonic ester synthesis?arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning