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The NMR spectra of the product from elimination of HCl from 2-chloro-4,4- dimethylpentane (1) can distinguish between the possible isomeric alkene products (2), (3) and

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The NMR spectra of the product from elimination of HCl from 2-chloro-4,4- dimethylpentane (1) can distinguish between the possible isomeric alkene products (2), (3) and (4) shown in Equation 1. Hb Hb H3C Ha KOH (i) Ha (1) (2) (3) (4) Equation 1 For each compound (2), (3) and (4) state the number of unique signals in the 'H NMR spectrum unique signals in the PC NMR spectrum negative intensity signals in the DEPT-135 spectrum signals in the DEPT-90 spectrum. . Construct and fully label a splitting diagram to account for the multiplicity of the signal expected for the methyl protons shown in bold, CH3, in structure (1). Explain how the coupling data for the Hb proton can distinguish between structures (3) and (4). Draw and label the predicted 'H NMR spectrum of structure (3). Predict means indicate approximate chemical shift position, multiplicity and relative integration for each of the expected signals

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