Indicate the most probable major products that are formed when treating the following haloalkanes with sodium ethoxide in ethanol or with potassium tert-butoxide in 2-methyl-2-propanol. a) chloromethane, b) 1-bromopentane, c) 2-bromopentane, d) 1-chloro-1-methylcyclohexane, e) (1-bromoethyl)cyclopentane, f) (2R,3R)-2-chloro-3-ethylhexane .

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Chloromethane cannot remove by lacking the b -carbon. Even hindered bases such as potassium tert-butoxide give substitution with this type of substrate.
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Sodium ethoxide gives S N 2 with primary substrates, while potassium tert-butoxide gives mostly elimination (E2).
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The ethoxide subtracts the innermost hydrogen from the molecule, forming the more stable alkene (thermodynamic product). This reaction is said to follow Saytzev's rule.
Potassium tert -butoxide is a hindered base that removes the most accessible hydrogen faster, forming mainly the less stable alkene (kinetic product). This reaction is said to follow Hofmann's rule.
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