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Organic Chemistry Questions F G H

e, Draw the skeletal structure of and categorize the following substrates which you will use in this experiment as a primary, secondary, tertiary, or aryl halide. 2-chlorobutane 2-bromobutans 1-chlorobutane 1-bromobutane bromobenzene f. Draw the SN2 mechanism of the reaction between (S)-2-bromobutane and iodide ion. Show lone pairs, electron pushing arrows, 3-D view to reflect appropriate stereochemistry, reactants, transition states, and products. Name the product. Draw and completely label a reaction energy diagram corresponding to the mechanism you have drawn g. Draw the S mechanism of the reaction between 2,5-dimethyl-2,5-hexanediol and hydrochloric acid (excess). Show lone pairs, electron pushing arrows, 3-D view to reflect appropriate stereochemistry, reactants, intermediates, and products. You do not have to show transition states. Name the product. Draw and completely label a reaction energy diagram corresponding to the mechanism you have drawn. Page 2 of 4 4/22/18

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(i) I- chloschutane CH CH 38 ii)2- chloo budane CH CH H, C ce SEcONDAR (iv) R-8omobutane CH HC CM tomobenene CARYLANSWeR CH .cH3 CM. Ch CH, CH CS3-2-8somobutare CH

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