Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 18, Problem 56DSP
Interpretation Introduction
Interpretation:
The identity of the compound X in the given sequence of reactions, isto be determined.
Concept Introduction:
During the Baeyer Villiger oxidation of
Usually, the oxygen atom is inserted between the carbonyl and the larger of the two groups attached to the carbonyl.
The ketone is converted to the conjugate acid of the ester. Further hydrolysis of the conjugate acid forms the ester.
The peroxy acid used is converted to the corresponding
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
An esterification and a claisen condensation are the reverse of each other. Write a single equilibrium reaction that is appropriate for both reactions and discuss the experimental conditions that can drive this equilibrium toward one side or the other of this reaction.
The reactions are:
Esterification Reaction: acetic acid is reacted with methanol and sulfuric acid catalyst under heated conditions to produce methyl acetate.
Claisen Condensation: methyl acetate is reacted with water and sulfuric acid catalyst under heated conditions to produce acetic acid
Which of the following statements is INCORRECT?
a. The electronegative oxygen atom of the α,β-unsaturated carbonyl compound withdraws electrons from the β-carbon leading to more electron-poor characteristic for the carbon than a typical alkene C=C bond.
b. A carbon–oxygen double bond is structurally similar to a carbon–carbon double bond.
c. Aldehyde and ketones usually react irreversibly with alcohols or water to yield acetals or vicinal diol respectively.
d. The carbonyl carbon atom is sp2-hybridized and forms both sp2 σ-bond and a p π-bond to oxygen.
In biochemical reactions, decarboxylation of carboxylic acids typically takes place for-keto carboxylic acids. Justify a rational why nature opted for-keto carboxylic acid decarboxylation.
Among the following types of biochemical reactions, ester hydrolysis, rearrangement reactions, water elimination reactions, and anhydride hydrolyses, which one is the most favorable one. Rank the above reactions types in the order of being the most to least favorable reaction
Chapter 18 Solutions
Organic Chemistry - Standalone book
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.3 - Prob. 3PCh. 18.4 - Prob. 4PCh. 18.4 - Prob. 5PCh. 18.6 - Prob. 6PCh. 18.7 - Prob. 7PCh. 18.7 - Prob. 8PCh. 18.7 - Prob. 9PCh. 18.8 - Prob. 10P
Ch. 18.8 - Prob. 11PCh. 18.8 - Prob. 12PCh. 18.9 - Prob. 13PCh. 18.10 - Prob. 14PCh. 18.10 - Prob. 15PCh. 18.11 - Problem 18.16 The product of the following...Ch. 18.11 - Prob. 17PCh. 18.12 - Problem 18.18 What other combination of ylide and...Ch. 18.12 - Prob. 19PCh. 18.12 - Prob. 20PCh. 18.12 - Prob. 21PCh. 18.13 - Prob. 22PCh. 18 - (a) Write structural formulas and provide IUPAC...Ch. 18 - Each of the following aldehydes and ketones is...Ch. 18 - The African dwarf crocodile secretes a volatile...Ch. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Prob. 29PCh. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - Each of the following reaction has been reported...Ch. 18 - Prob. 33PCh. 18 - On standing in 17O-labeled water, both...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - The OH groups at C-4 and C-6 of methyl ...Ch. 18 - Prob. 38PCh. 18 - Prob. 39PCh. 18 - The sex attractant of the female winter moth has...Ch. 18 - Prob. 41PCh. 18 - Prob. 42PCh. 18 - Prob. 43PCh. 18 - Suggest a reasonable mechanism for each of the...Ch. 18 - Prob. 45PCh. 18 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Prob. 49PCh. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Prob. 52DSPCh. 18 - Prob. 53DSPCh. 18 - Prob. 54DSPCh. 18 - Prob. 55DSPCh. 18 - Prob. 56DSPCh. 18 - Prob. 57DSPCh. 18 - Prob. 58DSP
Knowledge Booster
Similar questions
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardRecalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing functional group.arrow_forwardEarly organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.arrow_forward
- The reaction between propanoic acid and benzyl alcohol in an acidic medium. Show the product by writing the reaction together with its mechanism.arrow_forwardDraw structural formulas for the hemiacetal and acetal formed from the reagents. The stoichiometry of reaction is given in the problem.arrow_forwardSome alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.arrow_forward
- Write the reaction flow chart fir the following condensation and further heating of resulting productsarrow_forwardUsing chemical structures draw the complete chemical reaction of Acetone with benzaldehyde under basic conditions, provide both the major and minor products.arrow_forwardOn synthesis of esters via nucleophilic acyl substitution: How is excess alcohol eliminated from the crude product? Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.arrow_forward
- 1-Explain oxidative and reductive Ozonolysis 2- Give the sequence of the relative reactivities of carboxylic acid derivatives. Explain why acyl chloride can be converted into ester but ester cannot be converted into acyl chloride 3- Write the product when ester of propionic acid, propionyl chloride and propanal reacts with excess of methyl magnesium bromidearrow_forwardX Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►arrow_forwardIn an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol. Ethanol is often present in the technical grade of diethyl ether. If this grade rather than anhydrous were used, what effect, if any, would the ethanol have on the formation of the Grignard reagent? Explain.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher: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