(iv) Show both resonance canonical forms describing the bonding in enolate C. Use these diagrams to explain why enolates are examples of "ambident" nucleophiles.

Chemistry
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Chapter1: Chemical Foundations
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PLEASE JUST ANSWER THE LAST PART (IV)

(i) Ketone A forms small amounts of enol B under the conditions given. Identify enol B and
suggest a mechanism for its formation.
B
cat. HCI
H₂O
A
base
or
C
(ii) What is the outcome if the process referred to above in section (i) is conducted with DCI in
D₂O?
(iii) Enolate C can be formed in either equilibrium amounts, or quantitatively, depending on the
choice of base. Give an example for a suitable base for either case and provide a curly arrow
reaction mechanism for the formation of C.
(iv) Show both resonance canonical forms describing the bonding in enolate C. Use these
diagrams to explain why enolates are examples of "ambident" nucleophiles.
Transcribed Image Text:(i) Ketone A forms small amounts of enol B under the conditions given. Identify enol B and suggest a mechanism for its formation. B cat. HCI H₂O A base or C (ii) What is the outcome if the process referred to above in section (i) is conducted with DCI in D₂O? (iii) Enolate C can be formed in either equilibrium amounts, or quantitatively, depending on the choice of base. Give an example for a suitable base for either case and provide a curly arrow reaction mechanism for the formation of C. (iv) Show both resonance canonical forms describing the bonding in enolate C. Use these diagrams to explain why enolates are examples of "ambident" nucleophiles.
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