**Stork Enamine Reactions****Problem Statement:**Write the mechanism to predict the product of the reaction of acetone with diethylamine (using a Lewis acid catalyst), followed by warming with benzoyl chloride (PhCOCl), and then water.**Introduction:**The Stork enamine reaction involves the formation of an enamine from a ketone or an aldehyde and a secondary amine. This reaction is important in organic synthesis for forming carbon-carbon bonds.**Mechanism Steps:**1. **Enamine Formation:** - Acetone reacts with diethylamine in the presence of a Lewis acid catalyst to form an enamine. This step involves the removal of water and formation of a C=C-N bond.2. **Alkylation with Benzoyl Chloride:** - The enamine undergoes alkylation with benzoyl chloride. The nucleophilic enamine attacks the electrophilic carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate.3. **Hydrolysis:** - The final step involves hydrolysis of the intermediate to regenerate the carbonyl group and form the final product. Water is added to revert the enamine to the original carbonyl form, yielding the desired product.This stepwise process highlights the utility of Stork enamine reactions in complex organic syntheses, particularly in forming carbon-carbon bonds.

Answered: Image /qna-images/answer/085efe89-d620-4234-9b5c-0b7af28da618.jpg

Answered: Stork enamine reactions - Write the…

Stork enamine reactions - Write the mechanism to predict the product of reaction of acetone wi catalyst), following by warming with benzoyl chloride (PhCOCI) and the

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: (lewis acid catalyst) FeCl3 OH (acetone) OH (meso - hy dro benzoin) (2,2-dime thyl-4,5-1,3-dixolane)

A: The stereochemistry of products is very important in organic chemistry. The given reaction is very…

Q: a) Complete the mechanism of the initial step of the reaction of the alkyl halide with sodium azide…

A: Reaction mechanism of chlorocyclopentane with sodium azide is drawn as,

Q: 24) Upon azonolysis, compound X produces 2 compounds: Y and Z. can be prepared from the follory…

Q: # (g) (h) (i) (1) Th 2. H₂O Ol 1. NaBHA 2. H₂O (1) 2 eq CH₂MgBr (2) H₂O 1. CH₂MgBr ► А 2. H₂O MnO₂…

A: DIBAL H reducing agent used to form aldehyde from Ester .

Q: 21. Provide the structures of the organic products in the following reactions: Br HO (Z)-vinyl…

A: Given that, the reaction schemes are shown below We have to give the organic products of the given…

Q: complete the following scheme of reactions (Write the structures) from A to E KOH C Aldehyde A major…

A: Alkyl halide won reaction with alc. KOH undergoes beta-elimination to form alkenes. The alkene which…

Q: e pl OH 1) SOC1₂, heat 2) (CH₂)₂CHOH, pyridine.

A: Reaction:Product: Need to be determine

Q: P2/ Outline all steps in a possi ble laboratory Synthesis of ta following Compounds : (Using any…

Q: Which of the following compounds forms a ketone upon oxidation ?* (A) CH,OH (C) CHOH (E) (В) он (D)…

Q: Which of these reaction sequences would product benzoic acid? a) isopropylbenzene reacts with KMNO4…

A: Correct answer is (a), (c) and (d). Isopropyl benzene is oxidized by KMnO4 to produce benzoic acid.…

Q: Osaw the Yeaction mechanisms for the reduction NABHU g benzshenone using Reduction (o.138g) NABH4…

Q: ÇI OH O2N

Q: (a) NaCN (d) NEt H2SO4, 0°C dropwise EINH3 + (b) MEOH (exs.) (e) TSOH, toluene heat 1) Ph3P Br (c)…

Q: 1) Mg. 6ther HBr B 2) puis H,0

A: Markovnikov addition of alkene.

Q: 22- Give one example for the hydration of Alkene: That is the Addition of H2O by oxymercuration.…

A: To write the reaction of oxymercuration demurcuration and their Mechanism. To write the reaction of…

Q: boog gniw61b 1. The radical reaction results in an enol which then tautomerizes to the ketone. JUST…

A: Norrish type II reactions are photochemical reactions involving a γ-H abstraction by a carbonyl…

Q: 11. Methylation of sodium azide with trimethylsulfanium iun would give off gas: [a] dimethylsultide…

A: sodium azide (NaN3) undergoes methylation with trimethylsulfanium ion (Me3S+), it leads to the…

Q: 1. Predict the product and write the systematic reaction mechanism for the reaction of benzoic acid…

A: Carboxylic acids when treated with alcohols in presence of inorganic acid as catalyst results in the…

Q: 17. (5@; 20) Synthesis. Beginning with alcohols of FOUR carbons or fewer, OUTLINE syntheses of the…

A: There are many mechanisms in organic chemistry such as nucleophilic substitution, nucleophilic…

Q: Write the reagents/mechanisms/products of the following reactions. .COPH Weak base PHCHO (S)-proline…

Q: a) The scheme below shows the synthesis of a natural product: MgBr- он B ore CHO CHO Suggest…

A: In the sequence of the reaction in the first step addition of Grignard reagent on the carbonyl group…

Q: 1) NaOCH, 2) Н,О он OCH, OH OH OCH, он OCH, OCH3

A: According to our guidelines we can not provide the solution to another question. Please post the…

Q: NaH (A) CH,-(CH),I PI HBr (excess) OH NaOH МСРВА (B) CH;Cl, PII H,SO, MeOH EtOH PIV PIII…

A: PI : There are two products formed. Since the HBr is in excess amount so it will lead to alkyl…

Q: tructure of I drow th lectrophilic Salicyls enation( ch tion. nonation. dal caraft lal craft

A: The structure and reactions of Salicylic acid, (2-hydroxybenzoic acid) are as follows;

Q: -Enal is a composand derived from ethene by replacing hydrogen atom by hydivaay group one af the…

A: Enol is derived from ethene by displacing H atom. Enol has OH group and alkene group.

Q: pyrrolidine are important intermediates in the synthesis of 1,5-diketones. (1st pic) On the…

Q: (A) Coz E ✓C0267 8. (B) 1. NabEt, Ero 2. H₂O, A ericana Co₂Lt (D)

Q: A. Reaction with Nitrogen Compounds; Write whether the following aldehydes and ketones are positive…

A: A. The aldehydes and ketones considered are not positive species. But have polarized carbonyl bonds…

Q: Concept Questions Predict the Product. Predict the major organic product(s) for the following…

A: The question is based on organic reactions. We need to identify the product and explain its…

Q: Predict the organic product of the following reaction. OH PBr3 draw structure

A: Alcohol reacts with phosphorus trihalide to form alkyl halide through SN2 pathway.

Q: CONCEPT QUESTIONS Predict the product. Predict the major organic product(s) for the following…

A: The question is based on organic reactions. We need to identify the product and explain its…

Q: On reacting acetaldehyde with a large excess of formaldehyde in the presence of a base,…

Q: Identify the product of the following: H₂ in Pt KMnO4, warm H₂SO4 HgSO4 C6H5MgBr then H3O+ H₂CrQ₁ ag…

A: Acids are used to donate a protons. Bases are used to abstract a proton. The nucleophiles are…

Q: 2. Predict the organic product from each of the following reduction reactions. (a) O OH OMe NaBH4 A…

A: NaBH4 ---> Reduces aldehyde and ketone to alcohol NaAlH4 ---> Reduces aldehyde, ketone, ester…

Q: 4) By , sabrti fu fira reaption predicl and is added H"eductwtdicy is added H the H. a) 2 maythigl…

A: Since, you have asking to solved multiple questions, so I will solved first one question for you.…

Q: give the relative reaction rate of the following acid derivatives when reach with an amine, and your…

Q: C. b. d. HN a. 4. Predict-the-Product ). Draw the structure(s) of the major organic product(s)…

A: The question is based on organic reactions. we need to identify the product formed and explain…

Q: 27 An alkent on ozonolysis pave etlianal and propanone. The alkene could be A) Hut-2-ene B)…

A: Organic reaction mechanisms: As per our guidelines we have to answer first question only

Q: pLEASE PROVIDE DETAILED SOLUTION AND GIVE THE EXP;ANATION OF CORRECT AND INCORRECT OPTION...

Q: Alcohols react with acyl chlorides in the presence of tertiary amines to yield esters.' As described…

Q: Select the method that would be successful in producing the product starting from the given reactant…

A: Here out of two esters one is replaced by acid that means there is hydrolysis and other one is…

Q: the following Reactions (i) and (ii) to answer Questions 40 - 42. ) R- a. R- it is the Product X or…

Q: В. С. :CI;

A: Halogenation of carboxylic acid at alpha- position is known as Hell-Volhard Zelinsky Reaction or…

Q: a) H₂SO (cat.), H₂O b) workup Q11 Provide all carbon containing products

A: Step 1: Starting material: CH2=CH−CH2−N(CH3)−CH2−CH3 (an allylic amine)reaction conditions: a)…

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

**Stork Enamine Reactions**

**Problem Statement:**

Write the mechanism to predict the product of the reaction of acetone with diethylamine (using a Lewis acid catalyst), followed by warming with benzoyl chloride (PhCOCl), and then water.

**Introduction:**

The Stork enamine reaction involves the formation of an enamine from a ketone or an aldehyde and a secondary amine. This reaction is important in organic synthesis for forming carbon-carbon bonds.

**Mechanism Steps:**

1. **Enamine Formation:**
- Acetone reacts with diethylamine in the presence of a Lewis acid catalyst to form an enamine. This step involves the removal of water and formation of a C=C-N bond.

2. **Alkylation with Benzoyl Chloride:**
- The enamine undergoes alkylation with benzoyl chloride. The nucleophilic enamine attacks the electrophilic carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate.

3. **Hydrolysis:**
- The final step involves hydrolysis of the intermediate to regenerate the carbonyl group and form the final product. Water is added to revert the enamine to the original carbonyl form, yielding the desired product.

This stepwise process highlights the utility of Stork enamine reactions in complex organic syntheses, particularly in forming carbon-carbon bonds.

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

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 2 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

Propose an efficent synthesis.
4. Provide an alternative method for the preparation of cyclohexene from another compound than cyclohexanol. Give a reaction equation only D, Focus nited States) oto acer
Write down the reduction reaction of each molecule using appropriate reagents, listing the follo compounds according to their of reduction
Q4. Unsaturated carboxylic acid, I, can be prepared in two-steps form aldehyde K. From I, FGI leads to ester J, which then can be disconnected. In the forward sense the preparation of J involves a Wittig reaction. CO₂H J CO₂Et K + Phosphorus ylide (a) How do you convert esters into carboxylic acids (reagent(s), mechanism not required)? (b) Give a retrosynthesis of J leading to the aldehyde K and a phosphorus ylide. (c) Trace your ylide back to triphenyl phosphine and ethyl bromoacetate, giving reaction mechanisms for the forward sequence to give ester J.
Predict the principal organic product(s) for each of the following reactions
Please help with this question question 9
Arrange the following in compounds in INCREASING reactivity to hydrolysis. ororon ABC DEF -NH₂ GHI INCREASING REACTIVITY TO HYDROLYSIS: choose your answer... < choose your answer... choose your answer...
How would I produce ethoxybenzene from benzene
Please provide only typed answer solution no handwritten solution allowed
Draw the structure of the major organic product(s) of the reaction. Please give clear and detail image
Give the major organic product(s) for each of the following reactions. The topic is “reactions of alkynes”
1