Reaction of pentanoyl chloride (CH3CH2CH¿CH¿COCI) with lithium dimethyl cuprate [LiCu(CHa] forms a compound J that has amolecular ion in its mass spectrum at 100, as well as fragments at m/z = 85, 57, and 43 (base). The IR spectrum of J has strongpeaks at 2962 and 1718 cm1. Propose a structure for J.

MASS SPECTRUM: Mass spectrum is used to analyze chemical compounds with the help of mass to charge…

Answered: Reaction of pentanoyl chloride…

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.20P

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Reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2] forms a compound J that has a molecular ion in its mass spectrum at 100, as well as fragments at m/z = 85, 57, and 43 (base). The IR spectrum of J has strong peaks at 2962 and 1718 cm-1. Propose a structure for J.
Treatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at m/z = 142 (M), 144 (M + 2), 129, and 127. P has absorptions in its IR spectrum at 3096–2837 (several peaks), 1582, and 1494 cm-1. Propose possible structures for P.
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?
Treatment of 2-butanone (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (>1500 cm–1 only) and 1H NMR spectrum of Q are given below. What is the structure of Q?
Propose a structure for a compound that displays the given spectroscopic data. The molecular ion in the mass spectrum appears at m/z = 116. IR: 1710 (s) and 3000 (s, broad) cm¹. ¹H NMR: 8 = 0.94 (t, J = 7.0 Hz, 6H), 1.59 (m, 4H), 2.36 (quintet, J = 7.0 Hz, 1H) and 12.04 (broad s, 1H) ppm. 13C NMR: 8 = 11.7, 24.7, 48.7, and 183 ppm. Deduce the structure. Select 11 ||| ||| Q Search Draw C H O • Templates More Question Source: Vollhardt 7e - Organic Chemistry: Structure And Function P W Erase Publisher: W.H. Freeman ENG 4: 4/18
G.5 Mass spectra were acquired for 1,4-diethylbenzene and 1-methyl-4- propylbenzene. The base peak of spectrum A is at m/z = 105 and that of spectrum B is at mlz = 119. Match each spectrum to its compound.
2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?
The mass spectrum of 3-ethyl-3-methylheptane [(CH3CH2)2C(CH3)CH2CH2CH2CH3] shows fragments at m/z = 127, 113, and 85. Propose structures for the ions that give rise to these peaks
Identify the structures (molecular formula C9H10O). I R peak at 1688 cm−1; 1H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).
The mass spectrum of the following compound shows fragments at m/z= 127, 113, and 85. Propose structures for the ions that give rise to thesepeaks.
In the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH) was allowed to stand and a new compound L was formed. L has a molecular ion in its mass spectrum at 90 and IR absorptions at 2992 and 2941 cm−1. L shows three signals in its 13C NMR at 19, 52, and 101 ppm. The 1H NMR spectrum of L is given below. What is the structure of L?

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