Using the curved-arrow notation, provide mechanisms for each of the reactions given in Fig. P22.87. H3C C-CH3

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Using the curved-arrow notation, provide mechanisms for each of the reactions given in Fig. P22.87. H3C C-CH3 (c) (b) BrCHCO,CH3 I (CH)3 T BrCHCO,CH3 2 COEt KCO3 COEt NaOEt + 2 NaH HO CH3 DMF HO, H3O+ heat

(d) (e) 2 CH=0 CH=0 (CH3)2CHCOEt LICHIA THF -90 C acid KOH HC CH3 OH

OEt T COEt+H3C-C-CH3 Figure P22.87 NaOEt HO + HC || HOC-C CH C-COH chelidonic acid

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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Question Posted: Dec 07, 2023 05:21 AM

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Using the curved-arrow notation, provide mechanisms for each of the reactions given in Fig. P22.87. H3C C-CH3

Question:

H3C C-CH3 (c) (b) Br—CH—CO,CH3 I (CH₂)3 T Br–CH–CO,CH3 2 CO₂Et K₂CO3 CO₂Et NaOEt + 2 NaH HO CH3 DMF H₂O, H3O+ heat CO₂CH3 CO₂CH3

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a b This is an aldol addition dehydration cannot occur because the resulting alkene would violate Bredts rule The mechanism below begins with the enolate ion of the methyl ketone which is formed when ...View the full answer

Organic Chemistry

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