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Reaction of pentanoyl chloride
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- 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.arrow_forwardReaction 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?arrow_forwardMass spectra of butylcyclopentane and tert-butylcyclopentane were acquired. Spectrum A exhibited significant mass peaks at m/z values of 126, 97, 83, 69, 55, and 41. Spectrum B exhibited significant peaks at m/z values of 111, 69,57, and 41. Match each spectrum with its compound.arrow_forward
- b) The mass spectrum of shows three major peaks at m/z = 58, 43,and 15. What is the molecular ion peak for this compound? What are possible structures of the fragments? c) The IR show a large stretch at 1710 cm1. What functional group is indicated by this stretch? Draw the compound.arrow_forwardTreatment 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?arrow_forward2,3-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?arrow_forward
- A compound displays a prominent peak at 3400 cm¹ in its IR spectrum. The mass spectrum has a molecular ion with m/z of 74. The base peak is at m/z = 45. Draw a structure that best fits this data. Drawing I Atoms andarrow_forwardCompound C shows a molecular ion at m/z 148 and other prominent peaks at m/z 105 and 77. Following are its infrared and 1H-NMR spectra. Q.) Account for the appearance of peaks in its mass spectrum at m/z 105 and 77.arrow_forwardReaction of pentanoyl chloride (CH3CH2CH¿CH¿COCI) with lithium dimethyl cuprate [LiCu(CHa] 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 cm1. Propose a structure for J.arrow_forward
- Identify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits peaks at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits peaks at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.arrow_forward1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).arrow_forward1) They were given a mysterious chemical by ASP Rinuprasad, coded as Compound X, which was believed to be a forbidden drug smuggled through KLIA airport. Little they know about the chemical from the convict. As competent officers, together they decided to run several spectroscopic and analytical tests to determine the molecular structure of Compound X. They managed to obtain the spectra and data of IR, 'H NMR (400 MHz in CDCI 3), 13C and DEPT (100.6 MHz in CDC13), COSY, HMQC, HMBC, mass spectrometry and elemental analyses. Determine the molecular structure and name of Compound X. IR SPECTRUM 2.5 100 3.0 4.0 5,0 6.0 7.0 8.0 9.0 10 12 15 2000 avenumber cm 1500 000 1000 1Η ΝMR 7.50 7.45 7.40 7.35 7.30 7.25 7.20 7.15 7.10 7.05 7.00 55 50 1.5 100 9.5 9.0 8.5 8.0 7.5 7.0 65 60 4.5 35 3.0 2.5 20 10 0.5arrow_forward
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