Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 22.7, Problem 13P
Interpretation Introduction
a)
Interpretation:
The
Concept introduction:Acetoacetic ester synthesis converts an alkyl halide in to a methyl
To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.
Interpretation Introduction
b)
Interpretation:
The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.
concept introduction: Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.
To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Prepare the following compounds starting from benzaldehyde and the appropriate ketone. Provide reactions for preparing the ketones starting from aromatic hydrocarbon compounds.
Predict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+
An acetal is hydrolyzed in acidic solution to an aldehyde or ketone plus two molecules of an alcohol.
draw structural formula of the aldehyde (or ketone) produced when the following acetal undergoes hydrolysis in acidic solution
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
Knowledge Booster
Similar questions
- What products are formed in the base hydrolysis of the ester shown below with NaOH? Sodium ethanoate and ethanol B) Ethanol and ethanoic acid Ethanoic acid and sodium ethoxide Sodium ethanoate and water Methanol and sodium propanoate CH, C-O-CH2-CH,arrow_forwardDrawing an Enol and a Ketone Formed by Hydration of an Alkyne Draw the enol intermediate and the ketone product formed in the following reaction.arrow_forwardName the carbonyl compound that would be formed by the complete acidic hydrolysis of the following hemiacetal/hemiketal or acetal/ketal: OH OCH₂CH₂CH₂CH₂CH3arrow_forward
- How would you synthesize diketones starting from acetoacetic ester?arrow_forwardName the following compound: O Butyl cyclohexanoate O Butanoic cyclohexanecarboxylic anhydride O Cyclohexyl butanoate O Cyclohexanoic butanoate O Butyl cyclohexyl anhydridearrow_forwardWhich of these is the most viable route for the preparation or synthesis of a carboxylic acid? O Alpha-carbon substitution of ketones O Oxidation of aldehydes O Nucleophilic acyl substitution of amides O Elimination of alcohols O Nucleophilic addition of ketonesarrow_forward
- Which one of the following carboxylic acid derivatives can undergo nucleophilic acyl substitution without the need of an acid to catalyze the reaction? O CH3C=N ОН `NH2arrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents.phenylhydrazine and weak acidarrow_forward
- Which of the following compounds will NOT undergo nucleophilic substitution reaction? O isopropanol propylene oxide Benzoyl chloride butanonearrow_forwardWhich of the following pairs of reagents are used to synthesize the ester below? ethanol + ethanoic acid butanol + ethanoic acid ethanol + butanoic acid butanol + butanoic acidarrow_forward1. Which pair of aldehydes can lead to the following product? 10% NaOH(aq) OH H 2 moles of propanal ethanal + butanal 2 moles of ethanal ethanal + propanalarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning