![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_largeCoverImage.gif)
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 10.SE, Problem 19MP
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Trending nowThis is a popular solution!
![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
CH3
Ph3P-CHCH3
H3C
H3C
Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to
an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine
oxide and an alkene.
Ph3P-CHCH3
H3C
The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as
butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene
:0:
CH3
Com
The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…
Which of the following statements is correct?
A) The haloform reaction proceeds under very difficult conditions and the yield is very low.
B) The haloform reaction is used only for the identification of compounds containing secondary alcohol groups.
C) Methyl ketones or alcohols are oxidized with halogens in acidic solutions to give carboxylic acids and the appropriate haloform product.
D) Enolate anions react rapidly with halogens to give alpha-halocarbonyl compounds.
Ph3P-CHCH3
H₂C
H3C
Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to
an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine
oxide and an alkene.
CH3
00
+
The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as
butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene
X m
CH3
The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z
isomers)…
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7barrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Br H₂C H3C 1. NaOEt 2. H₂O* 3. heat H₂C. OEt Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H X CO2 CH3 + EtOH :OH На CH3 CO2 CH3 CH3 CH3arrow_forward
- Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the pres- ence of furan, a tricyclic compound is formed. Propose a structural formula for com- pound A and a mechanism for the formation of the tricyclic product. COOH NANO, HCI + CO, + N2 NH2 Anthranilic acidarrow_forwardThe ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forwardDraw the major organic product obtained by reaction of benzoyl chloride with dimethylamine, (CH3)2NH.arrow_forward
- The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forwardAn oxirane reacts with methylamine to give a product "A". Then, "A" reacts with an oxirane to give "B", which further reacts with SOCl₂ to give a product "C". Identify product "C". H3C-N H3C-N H3C-N OH OH HC-N NHarrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forward
- Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forwardPropose a feasible synthesis for diphenylacetylene from bromobenzene. Draw the reaction scheme and briefly describe the reaction.arrow_forwardSuggest possible synthetic route for each of following transformations. Show the reagents,intermediates and products.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 LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305446021/9781305446021_smallCoverImage.jpg)
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License