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Elimination and Substitution

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Your given a cyclohexane ring with a dashed Chlorine at C1 and a wedged methyl at C1, also there is wedged methyl at C2 and C6. Thus making there no trans protons available on these carbons for elimination (except methyl connected to chiral carbon w/chlorine, I think) the questions requires you to determine Substitution products and Elimination products. The reagent is NaOH the solvent is H2O, I figured it can only undergo E2 since its tertiary substrate and since its a charged nucleophile it wont undergo Sn1 and Sn2(tertiary don't undergo Sn2) thus leading me to believe that E2 is only possible product, please help!!!! (our professor said charged bases/nucs. only undergo E2/Sn2 respectively) I hope that isn't too confusing, the product I got was a secondary substituted product (where chlorine and methyl were)

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This solution provides a detailed explanation of the given organic chemistry questions.

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Good morning, and good question!
You are correct that SN2 reaction is impossible, since it's a tertiary alkyl halide. Let's run through the other possibilities:
E2: You are correct about this one. Since the 1- and 6- carbons don't have an H opposite to the Cl leaving group, you can't get E2 products with the alkene in the ring. However, you can deprotonate the methyl attached to the 1-carbon, giving the ...

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