Question

Draw out a full mechanism for both an E1 and an E2 reaction. Use 2-bromohexane as your substrate, and be sure to draw BOTH major and minor products for each, labeling each accordingly

Using any reagent as long as it fits with the reaction.

Answer 1

The staucture ay Z-bromo herane is in BH сма - си, - си, - сну — си – си, For the elimination of suo mechanisms g bromo hexane ,theid is Ez-Mechanism All cue know that the to-Mechanism is single step : babe pulls a proton away from combon; simultaneously a halide ion departs and the double bond foums. Halogen talles its & pair with it, hydrogen leaves its e-paid behind, to form the double bondo what characteures this particular Nechanism is that they all happening simultaneously , in a single step, wa teansition state. U so

so, the reaction of 2-bromohexane with alcoholic kou followers Huo product Soumation by - mechanism. One product is neajou because of more staibility where as becand is rinon one because of less staibility . so, the mechanismi below or CH₂ - CH₂ - CH2 - CH2 - C1-C43 3 Bul (alc) koul CHO CH₂ - CH - CH 31 ] Cyta-c On kon Transition state Transition stat

Double C₂-CH₂ - CH₂ – CH=CH-CH2 2 - CH₂ - Cu =ch .ch - CH₂ - CH₂ -(4, -(ly-CH=CH Major product minon product Plastan -dene Hexa-l-ene. • Hena -g- ene å mome stable than dena-l-ene because nena-2-ene has sd-kydhogen which helps in providing more staibility to it by uppen conjugation effect where cas Hexa-d-ene has just tuo &- bly drogen and it provide it less staibility,

The E-Mechanism In In this mechonima the bond breaking this mechanism the electronic changes and bond-making - are the same as in Ea i hore howench, hey are taking place , not sinuultan cously, but one after the other where ta inuolues in a single stop, t kuo stebs. In Sheb © the substrate undergoes slow Retemo - |-lysis to fourm halide ion and a cambocation. In steep (2) the caubocation rapidly loses a puoton to the base and forms the alkene. So, the treatment of a buonohaane with n-Butylhynonides Follolod the E-mechanisme. C BHI Steeb CH₃ -CH₂-CH ₂ -CH2-CH=CH2 - & But CH₂ - CH₂ - CH₂ - C – Eu achiz Step 2 Ch & M2 - CH₂ - CH₂-cn- n-Bu Qo CH3 -CH2-CH2 – CH = CH – CH3 + CH3-CK-Colly - CH=CH2 Meron product, - Majoh Product 5-& hydrogen 2-01-hydrogen 1. Due to the mone artyduogen hera-2-ene is more stable than the hexan - kene because of by benconjugation.
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