Reaction of 2-methylpropanoic acid [(CH3)2CHCO2H] with SOCl2 followed by 2-methylpropan-1-ol forms X. X has a molecular ion at 144 and IR absorptions at 2965, 2940, and 1739 cm-1. Propose a structure for X.

Reaction of 2-methylpropanoic acid [(CH3)2CHCO2H] with SOCl2 followed by 2-methylpropan-1-ol forms X. X has a molecular ion at 144 and IR absorptions at 2965, 2940, and 1739 cm-1. Propose a structure for X.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 46AP: Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of...

See similar textbooks

Related questions

Q: Ozonolysis of an unknown compound gave formaldehyde (H;C=0), ethanal (CH3CHO), and 2-oxopropanal…

A: Ozonolysis of alkene yield carbonyl compounds.

Q: Cleavage of oct-1-ene with hot, KMnO4 will yield _____________. octanol and carbon dioxide…

A: The question is based on the concept of organic reaction. It is the Oxidation reaction of alkene…

Q: (stereochemistry)

A: We have to draw the structure of syn and anti addition of Br2

Q: *19. Following are the NMR spectra of three isomeric esters with the formula C;H14O2, all derived…

A: First we have to calculate the double bond equivalence (DBE) of the moleculer formula C7H14O2 by…

Q: Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in…

A: Two different chiral diethyl tartrate isomers, (+)-DET and (-)-DET are used to indicate the…

Q: 2.11. 1,2-Diphenyl-1-propanol can be prepared by hydride reduction of 1,2-diphenyl- 1-propanone or…

Q: Propose possible structures for compounds given the closed formula by analyzing the infrared…

A: Analysis of Ir spectrum

Q: 7. (Chapter 15 - Q41a) Propose a structure for the compound that fits the following description.…

Q: 10. (a) Give reasons, arrange the following compounds in order of decreasing frequency of carbonyl…

A: This Question is based on IR Spectroscopy.

Q: A solution of acetone [(CH3)2C = O] in ethanol (CH3CH2OH) in the presence of a trace of acid was…

A: IR spectroscopy study the interaction of infrared radiation with matter. Its range for analysis of…

Q: The p-toluenesulfonate derived from (R)-2-octanol and p-toluenesulfonyl chloride was allowed to…

A: (R)-2-octanol and p-toluenesulfonyl chloride reacts to form a torsylate group, as the hydrogen from…

Q: Treatment of 1-pentene with H2SO4/H2O gave product D. The MS spectrums of Compound D is shown below.…

A: Mass spectrometry is an analytical technique which is used to measure the mass-to-charge ratio of…

Q: The reactant shown, having an axial p-toluenesulfonate in its most stable conformation, undergoes…

A: Cyclohexane undergo elimination reaction in presence of base if there is an anti H is present in…

Q: Propose a structural formula for compound A, C5H13N, given its IR and calculated 1H-NMR spectra.

A: The provided molecular formula of the compound is C5H13N. So, the double bond equivalent (DBE) = 5 –…

Q: 1. The sex attractant for the common housefly is a hydrocarbon with the molecular formula C23H46. On…

A: The molecular formula of the sex attractant for the common housefly is C23H46. First we have to…

Q: Compound A below is a key intermediate in the synthesis of keto-myo-inositol B. Suggest a synthetic…

Q: As reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in…

Q: 7. An unknown amine X has the molecular formula C8H₁7N. Treatment of amine X with excess CH31…

A: Here an unknown amine X( C8H17N) when undergo Hoffman exhaustive methylation followed by…

Q: A C5H3 alkyne is reacted with Lindlar's catalyst and hydrogen gas to yield product with the…

A: Molecular formula of alkyne = C5H8 Alkyne on reaction with lindlars catalyst gives cis alkene

Q: As we will learn in Chapter 17, reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D,…

A: In this reaction, Acetone reacts with lithium acetylide and tetrahedral lithium anion is formed,…

Q: 12. When 1-chloronaphthalene is treated with sodium amide, Na+NH2 , in the presence of piperidine,…

A: Here we have to explain the mechanism of reaction when 1- chloronaphthalene react with piperidine in…

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

Q: 1-Phenyl-2-butene has an ultraviolet absorption at Amax = 2.08 nrn (ɛ = 8000). On treatment with a…

A: Spectroscopy is based on the interaction between light and matter. The principle of UV-VIS…

Q: The reaction of l2 with Na11BH4 yields a gaseous product with an empirical formula of BH3. a) Draw…

A: a) The gaseous product having monomer empirical formula is B2H6-diborane . b IIB NMR…

Q: Propose a structure for a compound C,H12O2 that dissolves in dilute NaOH and shows the followin 'H…

A: 1H NMR spectroscopy is used to predict the structure of compounds. The given molecular formula of…

Q: B-Damascenone belongs to a family of fragrant natural products called rose ketones that have been…

A: MCPBA is use for the epoxidation of alkene. MCPBA is electron deficient compound this it selectively…

Q: Compound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives…

Q: Write the mechanisms of those two reactions with explanation

A: The mechanism can be given as follows:- Quaternization reaction: In the given compound lone of N…

Q: Treatment of W with CH3Li, followed by CH3I, affords compound Y(C7H14O) as the major product. Y…

A: (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.

Q: . The preparation of the sex pheromone of the boll worm moth, (E)-9,11-dodecadien-1-yl acetate from…

A: Organic compound synthesis:

Q: Question is attached as a picture. Thank you!

A: Diels-Alder reaction:During this reaction, three pi bonds will get broken; two sigma bonds and one…

Q: A compound of formula C11H16N2 gives the IR, 1H NMR, and 13C NMR spectra shown. The proton NMR peak…

Q: b) Pyrrole and indole both react with the reagents shown below to give compounds E and F…

A: Pyrrole and indole both are undergoing electrophilic substitution reaction. We have to tell the…

Q: Choose the best set of conditions for a Friedel-Crafts acylation of aromatic compounds. A)…

A: Friedel-Crafts Reaction

Q: A retrosynthetic analysis of 1 was undertaken suggesting a forward synthesis starting from compounds…

A: We have to synthesize organic compound 1 :

Q: Direct Cross-Dehydrogenative-Coupling (CDC) between Benzyl Ethers and Simple Ketones: DDQ O-RI 100°C…

Q: M-C-H AICI3 t. HBr D + [o] room temperature (A)

Q: v) What products would you expect if 2-butyne were treated with ozone in the presence ofacetic…

A: Hello. Since your question has multiple sub-parts, we will solve first three sub-parts for you. If…

Q: Compound x (CeH12 reacts with BH3 followed by H2O2. NaOH, H20 to yield Compound Y (CgH140) as the…

Q: Which of the following compounds produce the 3 products shown on reaction with KMnO4 and acid (H+).…

Q: b) Compound E with a molecular formula of CAH&O gives a positive iodoform test. он H3C. NABH4 E CH3…

A: NaBH4 is reducing agent...it specifically reduce aldehyde and ketone into respective alcohol...…

Q: spectrum of A has a strong band near 171io cm-1. The broadband carbon NMR spectrum given below. a)…

A: As you have posted more than one question, we are doing first one for you . To do the rest repost…

Q: Indene NH4Br, KHSO5, CH3CN:H₂O Br OH or "Bromoindanol" OH Br You will determine the structure of…

A: This occur via bromonium intermidiate

Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

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

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

Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.
Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?
Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.
Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.
Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?
3. Propose a structure for Compound X which has a molecular formula C1oH12O with an IR absorption at 1687 cm-1. The 'H NMR spectrum of O is given below. 'HNMR of Compound X 3H зн 2H 2H 5H 8 7 6 5 3 2 ppm
Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.
Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products(M and N) with molecular formula C6H12. The 1H NMR spectra of M and Nare given below. Propose structures for M and N, and draw a mechanismto explain their formation.
Treatment of benzaldehyde (C6H5CHO) with Zn(Hg) in aqueous HCl forms a compound Z that has a molecular ion at 92 in its mass spectrum. Z shows absorptions at 3150–2950, 1605, and 1496 cm-1 in its IR spectrum. Give a possible structure for Z.
As reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?
There are several isomeric alcohols and ethers of molecular formula C5H12O. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppm Isomer B: δ = 1.19 (s, 9 H), 3.21 (s, 3H) ppm
Treatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of molecular formula C12H13DO3, which gave an IR absorption at approximately 1715 cm−1. What is the structure of B and how is it formed?