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 54DSP
Interpretation Introduction
Interpretation:
The configuration at the carbon in the product 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 carboxylic acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?
The Dess–Martin reaction reacts an alcohol with the Dess–Martin periodinane. The first step displaces one of the acetate groups on the periodinane with the alcohol. A base then deprotonates one of the alpha protons, forming a new carbonyl bond, iodinane and acetic acid. The oxidation stops at this stage to give the aldehyde.
Both Swern and Dess–Martin conditions will also convert a secondary alcohol to a ketone.
Now apply what has just been discussed.
Draw the major organic product.
Early 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.
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
- The compound 3,5,5-trimethyl-2-cyclohexenone can be synthesized using acetone and ethyl acetoacetate as sources of carbon atoms. New carbon-carbon bonds in this synthesis are formed by a combination of aldol reactions and Michael reactions. Show reagents and conditions by which this synthesis might be accomplished.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardMany types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who studied them. Propose mechanisms for the following named condensations: Perkin condensation: condensation of an aromatic aldehyde with a carboxylic acid anhydride Darzens condensation: Condensation of an α-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibuprofen. Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ster in the presence of an amine-caboxylic acid catalyst.arrow_forward
- The reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin. It Explain the reason by writing the reaction mechanisms of the reactions.arrow_forwardhe reaction that occurs when the benzaldehyde in your hand is reacted in a basic environment. Cannizzaro reaction is called benzoin recovery when reacted with cyanide. It Explain the reason by writing the reaction mechanisms of the reactions.arrow_forwardAcetal formation is a characteristic reaction of aldehydes and ketones, but not of carboxylic acids. Use retrosynthetic analysis to show how you could use a cyclic acetal protecting group in the following synthesis, then write equations for the procedure showing the necessary reagents.arrow_forward
- With organolithium and organomagnesium compounds, approach to the carbonyl carbon from the less hindered direction is generally preferred. Assuming this is the case, predict the structure of the major product formed by reaction of methylmagnesium bromide with 4-tert-butylcyclohexanone.arrow_forwardWhat functional group would be present in the product (the main organic product) of a reaction between a ketone and a Grignard reagent (with an acidic workup/quench)? Be specific (primary, secondary, tertiary).arrow_forwardThe Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group ofan aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur.The organozinc reagent is prepared by treating an a-bromo ester with zinc. Describe how each of the following compounds can be prepared, using a Reformatsky reaction:arrow_forward
- The following compound may be synthesized through alkylation of an appropriate enamine with an alkyl bromide, followed by hydrolysis of the resulting immonium ion. Using this strategy, provide the necessary starting materials for the synthesis. (Note that a portion of the starting enamine is given.)arrow_forwardDraw a structural formula for the product formed by treating reactants with sodium ethoxide in ethanol under conditions of the Michael reaction.arrow_forwardGive all possible and complete reaction for the following. Properly name the organic compound. 1. Oxidation of 2,4-pentanedione 2. Addition of Grignard reagentsarrow_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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning