Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane (CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm−1. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.

Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane (CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm−1. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

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

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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

Reaction of tert-butyl pentyl ether [CH₃CH₂CH₂CH₂CH₂OC(CH₃)₃] with HBr forms 1-bromopentane (CH₃CH₂CH₂CH₂CH₂Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm⁻¹. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.

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