Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its 13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that product. NH3 ? 5.8 5.7 2.2 7 6 Chemical shift (ppm) 10 9. 8 4 3 2 1

Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its 13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that product. NH3 ? 5.8 5.7 2.2 7 6 Chemical shift (ppm) 10 9. 8 4 3 2 1

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: A student exposed R-1-bromo-2-propanol to sodium hydroxide, isolated an optically active product,…

A: The question is based on the concept of the reactions. we need to identify the product formed in…

Q: 3. Propose a plausible mechanism for the following transformation: س & H₂N CF3 N H CN CF₂ OH

A: We have to draw the mechanism for the given transformation.

Q: Explain why protonating aniline has a dramatic effect on the compound’s UV spectrum, whereas…

A: Protonation is the addition of a proton molecule to make a conjugate acid. Each and every structure…

Q: A compound (CgH,NO) gives the following NMR data. In the box below please draw the structure of the…

A: Number of signals in 1H NMR = Number of sets of protons in different electronic environment Number…

Q: Provide an arrow pushing mechanism for the following reaction. Include protons and each step clearly…

Q: Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula…

A: The structure of F formed from the following conversion has to be proposed:

Q: Provide a detailed arrow-pushing mechanism for the following transformation: Me PHOH PhO. Et Мe Me…

Q: Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô…

A: The objective is to find the structure of compounds; A and B along with their formation mechanisms…

Q: Identify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent…

A: Addition of a molecule over a double bond is called addition reaction. After addition of HCl, three…

Q: 11 10 9 8 7 6 ppm 1H1H 5 4 2Н 3 ЗН 2 О

A: The question is based on the concept of organic spectroscopy. We need to analyse the spectral data…

Q: A compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by…

Q: When compound Y undergoes ozonolysis, a single product, Z, is produced. Which of the following is…

A: After analysis of all options, D option is incorrect beacuse no acid is present.

Q: Predict the major product for the following reaction sequence. CI 1) LIAI(OR) H ? 2) EtMgBr 3) H₂O+

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

Q: 15) What compound is produc 'N s treated with LiAlH4? -) CH3CH2CONH2 OCH3CH2CH2NH2 O CH3CH2CH2OH…

A: -> LiAlH4 is reducing agent which can reduce amide to amine .

Q: Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in…

A: a). Structure of A: The lack of IR absorption suggests the absence of CO bond and NH bond or OH…

Q: Provide an arrow pushing mechanism for the following reaction. Include protons and each step clearly…

Q: Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene…

Q: Two products are obtained from the reaction of (Z)-pent-2-ene with water in sulfuric acid. The mass…

Q: Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in…

A: In order to determine the compound structure, IR spectrum and proton-NMR spectrum are utilized. The…

Q: 3) Consider the chemical transformation below. RCO3H a) Predict the major product of the reaction by…

A: The given reaction is called an organic synthesis reaction, and it is a type of oxidation…

Q: Mustard gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard…

A: Sulfur in mustard gas is more nucleophilic than other corresponding oxygen compounds. This is due to…

Q: When propenal is treated with sodium acetylide, a product is formed whose IR spectrum exhibits a…

Q: When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR…

Q: Select the reagents that will allow the following transformation(s) to occur. -H ? 1) NaOH 2) propyl…

A: The transformation reaction from propyne (also known as methyl acetylene) to hex-2-yne involves…

Q: O 1) NaOEt 2) Q CH₂CH3 3) H3O+

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

Q: When phosgene is treated with excess methanol, a product is formed whose "H NMR spectrum shows one…

A: When phosgene is treated with excess methanol a product is formed whose 1H NMR spectrum shows one…

Q: Propose a structure for a C,H5O,N compound that is unstable in aqueous acid and has the given NMR…

A: C6H15O2N

Q: Rank the following proton descriptions for the major methyl nitrobenzoate product. H O₂N. OCH 3 * H…

A: Electron withdrawing groups pull electron density from benzene ring and therefore deshield the…

Q: The following three-step reaction was carried out on an unknown reactant to produce a product with…

A: Solution -

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: 1. NaOH OH 2. PHPH Br

A: The given transformations involves a phosponium ylide intermediate which react with carbonyl…

Q: НО

Q: ОН

A: Alcohols can be converted to corresponding alkanes. This can be achieved either by (i) converting…

Q: What phosphonium ylide reagent and what carbonyl compound react in THF solvent to form the molecule…

A: Product of following reaction can be made by applying appropriate reaction mechanism.

Q: 3) Consider the chemical transformation below. RCO₂H a) Predict the major product of the reaction by…

A: The given reaction is called an organic synthesis reaction, and it is a type of oxidation…

Q: Please Draw the structure of the compound with all the data below and label the structure with it…

A: Given: The formula of the compound: C9H9NO3 There are 7 C-NMR signals H-NMR data: 12.7 ppm, s, 1H…

Question

Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its
13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that
product.
NH3
?
5.8
5.7
2.2
7 6
Chemical shift (ppm)
10
9.
8
4
3
2
1

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Trending now

This is a popular solution!

Step by step

Solved in 4 steps with 4 images

SEE SOLUTION Check out a sample Q&A here

Similar questions

A reaction between benzene and unknown reagents gives a substituted product with the molecular formula C9H12. The product has the following ¹H NMR signals: 7.289 ppm (2H, triplet), 7.231 ppm (2H, doublet), 7.179 (1H, triplet), 2.901 (1H, septet), 1.253 (6H, doublet). → R a) Determine the product using the given ¹H NMR data. b) Propose the set of reagents used to give the product.
Provide the correct product for the following series of transformation. Hint: The product has a H NMR spectrum with only 2 resonances with relative H integrations of 3:1. 1. Br2 2. 3 eq. NaNH2, NH3 3. CH3I ? Br. Br H3C CH3 A) CH3 C) CH3 B) D) =CH3 A B D
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.
Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm−1 in its IR spectrum. F also shows eight lines in its 13C NMR spectrum, and gives the following 1H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.
2) Identify the reagents you would use in order to synthesize the compound below via an imine formation reaction. Insert a single reagent in each box below. [H+]
Based on its 13C NMR spectrum, how many types of carbon (i.e., sets of equivalent carbons) are present in the unknown monosubstituted benzene starting material?
Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?
What main signals would you expect in the IR spectrum and in the NMR spectrum for 3- (4- (dimethylamino) phenyl) -3-hydroxy-1- (p-tolyl) propan-1-one?
4. The 1H NMR spectrum shown below corresponds to one of the molecules A-D. Identify the molecule and then provide the complete IUPAC name for the molecule. Don't forget about stereochemistry. он ÕH ÕH B D 11 10 8 6 5 1 'H NMR: 3.35 (1H, m), 1.66 (1H, m), 1.36 (9H, m, overlapping signals), 0.91 (6H, d), 0.90 (3H, t)
Propose a reasonable and detailed mechanism for the following transformation: OH concd H₂SO4 heat + H₂O
Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form a compound with molecular formula C11H14. What product is obtained from the Wittig reaction?
Draw the two possible intermediates for the attack of the nitronium ion on naphthalene including the important resonance structures. Which position is favored? Why?