Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. CH2N2, ether + N2 Draw the structure of the organic product(s) of the ring expansion of this compound: • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co Previous Next
Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. CH2N2, ether + N2 Draw the structure of the organic product(s) of the ring expansion of this compound: • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co Previous Next
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 45MP
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Transcribed Image Text:Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction
involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of
this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with
diazomethane yields cycloheptanone.
CH2N2, ether
+ N2
Draw the structure of the organic product(s) of the ring expansion of this compound:
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co
Previous
Next
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