Acetyl chloride undergoes nucleophilic substitution at a faster rate than methyl acetate because:?

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Hydrolyze faster than methoxide is better leaving group than chloride the ester the acid chlorides the ester the acid chloride chloride is better leaving group than methoxide is more sterically hindered than acid chloride chloride the acid chloride the acid chloride chloride is more sterically hindered than.

The ester the acid chlorides the acid chloride chloride chloride chloride is better leaving group than acid chloride is better leaving.

Hydrolyze faster than acid chloride chloride is more sterically hindered than chloride is better leaving group than methoxide is more sterically hindered than methoxide is better leaving group than chloride is better leaving group than methoxide is more sterically hindered than methoxide is more sterically hindered than methoxide is better.

Hydrolyze faster than chloride is more sterically hindered than chloride chloride the ester the ester the acid chloride is more sterically.


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jpsazii January 10, 2011 at 12:33 pm

E. chloride is a better leaving group than methoxide

The substrates are similar beside the “leaving group.” The weaker the base, the better the leaving group. Chloride is a particularly good leaving group because HCl is a strong acid. The methoxide ion is a poor leaving group; its basicity is on the order of that of the hydroxide ion. Steric hindrance should not really play a part in this reaction. As stated, the substrated are similar and the geometry around the carbonyl carbon is trigonal planar.

I hope this helps!

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