Question

In the presence of sodium ethoxide and ethanol, (R)–3-chloro-2-methylhexane can undergo an elimination reaction as well as the SN2 reaction. Complete the reaction mechanism for the major product of the reaction and draw that product of the elimination reaction.

Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the grid and connecting them with bonds and including charges where needed. Indicate the mechanism by drawing the electron-flow arrows on the molecules. Arrows should start on an atom or a bond and should end on an atom, bond, or where a new bond should be created.

E1 and E2 Reactions of Alkyl Halides 27 of 30 > H.C CHI H, C öl Na AOOOOOO Submit Previous Answers Request Answer 10360 X Incorrect; Try Again; 4 attempts remaining You neglected to indicate the fate of the electrons from the C-H bond when the proton is abstracted. Consider how the double bond is formed in the elimination reaction.

Answer 1

In the presence of sodium ethoxide and ethanol, (R)–3-chloro-2-methylhexane can undergo an elimination reaction as well as the SN² reaction.

There is Branching at the $\alpha$- or $\beta$ - carbon increases steric hindrance and significantly retards SN2 reactions.Branching at $\alpha$- or $\beta$ - carbon increases the rate of E2 reactions because : increased
stability of the alkene product. Methoxide ion has greater basicity ,thus greater the E₂ / SN₂ ratio.

Probable error in Your answer : You have shown movement of electrons from C-H bond by single headed arrow instead of double-headed arrow.

Mechanism:

ce Hal ICH3 ,CAR 니 대 Na Oct EtoH? -CH₂ 2-methyl-Hex-2-ene R-3-celoro-2-hethyl thexque Mechanism CH3 i E2 ch3 CH3 -CH3 - Net - -CHOH NO GO-CH3