SN1 reaction, products?

2-chlorobutane + CH3OH #->#

The solvent is CH3OH.
What products are formed, showing stereochemistry?

1 Answer
anor277
Jun 16, 2018

Would we not get the racemic ether?

Explanation:

You got (racemic) #"2-chlorobutane"#...and under #S_(N)1# conditions this would give...

#H_3C-C(Cl)CH_2CH_3stackrel(H_3COH)rarrH_3C-stackrel(+)CH-CH_2CH_3 + Cl^-#

Substitution would give the ether....

#H_3Cstackrel(+)CHCH_2CH_3+H_3COH rarr H_3C-stackrel("*")CH(OCH_3)CH_2CH_3+H^+#

Elimination would give the isomeric olefin...

#H_3Cstackrel(+)CHCH_2CH_3stackrel(-H^+)rarr H_3C-CH=CHCH_3#

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