Portions of a molecule which get in the way of the Bürgi–Dunitz trajectory will reduce the rate of the reaction. This is another reason why aldehydes react faster than ketones in the cyanohydrin reaction, or for other nucleophillic attacks on C=O.
Bürgi–Dunitz trajectory
This refers to the 107° angle attack of nucleophiles when they attack a carbonyl. It can be considered a compromise of two effects:
Portions of a molecule which get in the way of the Bürgi–Dunitz trajectory will reduce the rate of the reaction. This is another reason why aldehydes react faster than ketones in the cyanohydrin reaction, or for other nucleophillic attacks on C=O.
Portions of a molecule which get in the way of the Bürgi–Dunitz trajectory will reduce the rate of the reaction. This is another reason why aldehydes react faster than ketones in the cyanohydrin reaction, or for other nucleophillic attacks on C=O.
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Thank you! Great explanation!
ReplyDeleteThanks for u r explaination
ReplyDeleteAwesome explanation
ReplyDeleteThis is an explanation, which I have encountered very often. However, it is not fully correct. The antibonding pii star orbital has a node in the middle, which means that the lobes with opposite phases are leaning away from each other. Therefore the observed Bürgi-Dunitz angle is in fact the angle, which allows the maximal overlap of the HOMO of nucleophile with the LUMO (pii star) of the electrophile.
ReplyDeleteThanks for explanations
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