2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.) NHNH2 NH3 NH2-phenylindole + + + H2O

2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.) NHNH2 NH3 NH2-phenylindole + + + H2O

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.57P

See similar textbooks

Related questions

Q: In the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it…

A: Since O is an electronegative atom with lone pair present on it Hence it will take H+ from the acid…

Q: Show how the following compounds can be synthesized from benzene: a. N,N,N-trimethylanilinium iodide…

A: a. The synthesis of the given compound from benzene is given below. The given compound is, N,N,N…

Q: Complete the reaction and draw: Acetophenone reacts with phenylmagnesiumbromide in presence of H2O…

A: Given reaction condition: Acetophenone reacts with phenylmagnesiumbromide in presence of H2O and…

Q: Draw the products of the following reactions: a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl…

A: a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

Q: Treatment of benzene with sucdnic anhydride in the presence ofpolyphosphoric acid gives the…

A: The question is based on the concept of organic reactions. we have to write the mechanism for the…

Q: What reaction sequence would lead to the following transformation? O (1) Na/NH3(1) (2) NaNH2 (3)…

Q: Vanillin can be reacted with a number of ketones to give interesting aldol condensation products.…

A: option- D is correct

Q: 4-Methyl-2-pentyne gives which product upon bromination followed by KOHVethanoi? (1) (2) COOH (3)…

A: In this question, we have to find out the correct answer of given problem by the help of the…

Q: 2,4-Dinitrophenylhydrazine is frequently used for making derivatives of ketones andaldehydes because…

A: 2,4-Dinitrophenylhydrazine- 2,4-DNPH is red to orange solid. It is reacts with aldehydes and…

Q: Predict the products of the reaction of the below reagents with either acetophenone or…

A: Note: Since you have posted a question with multiple subparts, we will solve the first three…

Q: Which of the following reagents will not undergo a substitution reaction with the benzenediazonium…

A: this a substitution reaction of benzenediazonium chloride salt.

Q: Treatment of Compound E with sodium amide and then methyl iodide does not produce the desired…

A: -> NaNH2 is a base hence, it can abstract most acidic hydrogen from compound and generate…

Q: Which of the following reagents will not undergo a substitution reaction with the benzenediazonium…

A: Those reagents which show substitution reaction with benzenediazonium chloride salt are given below…

Q: 1 The reaction of an a-diketone with concentrated sodium or potassium hydroxide to give the salt of…

Q: Provide a detailed, stepwise mechanism for the acid-catalyzed formation of acetophenone dipropyl…

A: When ketone reacts with alcohol first it form hemiketal and then this hemiketal further react with…

Q: ČOEt 1. EtO-Na+ OEt 3. NAOH, H,O, heat EtO 4. HCI, heat 2-Carbethoxy- 4-Butanolactone…

Q: Which of the following starting materials and reagents would be best to produce a racemic mixture of…

A: Here we are required to find the Starting material for the synthesis of 3methyl 3 hexanol

Q: NH2 NHCOCH3 H/H2O (Hydrolysis) NO2 ÑO2 p-Nitroacetanilide (major) p-Nitroaniline

Q: It is possible to generate sulfur ylides in a manner similar to that used to produce phosphonium…

A: First, the sulfur ylide attacks the carbonyl carbon and forms an intermediate.

Q: NH2 HO Atenolol Tenormin® Below is a two-step reaction sequence. What are the steps in the…

Q: 2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as…

Q: Addition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-amine,some…

A: a). The addition of one equivalent of ammonia to 1-bromoheptane up to the formation dialkylamine is…

Q: Show the products from the reaction of p-bromoaniline with following reagents: a)CH3Cl(excess) b)…

A: In p-bromoaniline due to the presence of NH2 group, the compound is basic in nature, thus it does…

Q: Give the shortest route to produce the desired products 1. cyclobutanoic acid to ethyl-cyclobutyl…

A: 1. Cyclobutanoic acid on treatment with SOCl2/pyridine give corresponding acid chloride which on…

Q: Propose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give…

A: The addition of an alcohol functional group to carbonyl compounds such as aldehydes and ketones…

Q: CoA C11H1602 H3C

A: First of all the negative charge of enol attack on carbonyl carbon to form six member cyclic ring.…

Q: Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that…

A: The 1H NMR peak between 7-8 ppm signifies the presence of benzene ring. Triplet at approximately…

Q: b) Provide the synthons and synthetic equivalents for the following compounds. i) Synthons:…

Q: The condensation of pyrrolidine with acetaldehyde gives an enamine product. Select the best answer…

Q: Given this retrosynthetic analysis, propose a synthesis for the local anesthetic hexylcaine. N. + HO…

Q: The widely used anticoagulant warfarin (see "Chemical Connections: From Moldy Clover to a Blood…

A: Reagents: A Compound or mixture added to a system to cause a chemical reaction to take place. Aldol…

Q: Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 +…

A: When butyl methyl ether reacts with Lewis acid BBr3, then oxygen of ether attacks boron of the Lewis…

Q: Predict the products or the reaction of (i) phenylacetaldehyde and (ii) acetophenone with the…

A: Since you have posted a question with multiple sub-parts, we will solve the first three sub-parts…

Q: Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route…

A: There are number of functional group associated with organic compounds which impart specific…

Q: Show how you would synthesize 2-phenylethanamine (PHCH2CH2NH2) starting from the following reagents.…

A: In this question, we want to Synthesized the PhCH2CH2NH2 from the starting material ( which have…

Q: 3. What are the main products of reaction of the following with phenyl magnesium bromide followed by…

A: Since you have posted a question with multiple sub-parts, we will solve the first three subparts for…

Q: Select the expected product of the following reaction sequence. NaCN 1. LIAIH, THF DMSO 2. Hао Br…

A: For the given reaction in the first step SN2 reaction take place to form alkyl cyanide with…

Q: Predict the major product when each reagent reacts with ethylene oxide. (a) KCN (potassium cyanide)…

A: Concept introduction: Steps for writing a correct mechanism are shown below. The atoms that contain…

Q: Below is a reaction scheme for the transformation of 2-phenylethan-1-ol to the corresponding…

Q: Show how you would synthesize 2-phenylethanamine (PHCH2CH2NH2) starting from the following reagents.…

A: The reactant in d is an amide which can be named 3-phenylpropanamide. The product…

Q: Predict the mononitration products of the following compounds.(a) o-nitrotoluene (b)…

Q: The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene…

Q: (c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in…

Q: Specify the reagent you would use in each step of the following synthesis: step 1 step 2 CI Reagents…

Q: What is the major product(s) of each of the following reactions? a.…

A: Note: Since we only answer up to 3 sub-parts, we’ll answer the first 3. Please resubmit the question…

Q: 1. Predict the products or the reaction of (i) phenylacetaldehyde and (ii) acetophenone with the…

A: Organic reactions are those in which organic reactant react to form organic products.

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.
Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)

NHNH2 NH3

N
H
2-phenylindole

+ + + H2O

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1 : Solution :

VIEW

Step 2 : Solution :

VIEW

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

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

2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis. Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)
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. Draw the necessary enamine below.
Addition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-amine,some dialkylamine, some trialkylamine, and even some tetraalkylammonium bromide.(a) Give a mechanism to show how this reaction takes place, as far as the dialkylamine.
2,4-Dinitrophenylhydrazine is frequently used for making derivatives of ketones andaldehydes because the products (2,4-dinitrophenylhydrazones, called 2,4-DNP derivatives)are even more likely than the phenylhydrazones to be solids with sharp melting points.Propose a mechanism for the reaction of acetone with 2,4-dinitrophenylhydrazine in amildly acidic solution.
Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.
Draw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HCl
When phenylacetaldehyde (C6H5CH2CHO) is dissolved in D2O with added DCl, the hydrogen atoms a to the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.
Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base: (a) terf-butyldimethylsilyl chloride (TBS-C1] (b) triisopropylsilyl chloride (TEPS-C1) (c) triethylsilyl chloride (TES-C1)
-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.