Question

4. Fill-in-the-blanks: draw the missing reactants or products involved in the following single or multi-step reactions. Indicate stereochemistry and draw multiple stereoisomers where applicable. i EtOH EtOH [H2SO4] 1) EtMgBr 2) H20 5. For most ketones, hydrate formation is unfavorable, because the equilibrium favors the ketone rather than the hydrate. However, the equilibrium for hydration of hexafluoroacetone favors the hydrate. Propose a mechanism for this transformation below and provide an explanation for this observation. H2O Но он F3CX CF3 F3C CFR = -

Answer 1

4)

2 a) 04 OH 0 29 EtoH [H₂504] DELMg Br sem OH se 04 2) H.O H H₂0 oh oh crz Icf3 This compound is most elecmophilic compound. a R-TOH pec Roth ben HEX hoft nget f R- Come DCH 3 ng or 1 27 Ha ott R N-ome DCH. CH 3 Renome Weinreb amide de la escuela de

a) This is protection of ketone in presence of alcohol and acid to get hemiacetal as a product in racemic form.

b) This is Grignard rection ketone on reaction with Grignard reagent we will get tertiary alcohol in racemic form.

5) In Ditriflurometh ketone carbonyl carbon is very electron deficience because both -CF3 group pulling electron density towards themselves, so water will attack on carbonyl carbon and form hydrate which is stable than ketone.

2) In this three compounds aldehyde which is having two Fluorine atom at alpha carbon is most electrophilic because in other two compounds i.e. ketone is slightly electron rich due to hyperconjugation of methyl group and other aldehyde fluorine atoms are on bita carbon so that is also less electrophilic than first aldehyde.

3)

a) Primary alcohols on oxidation we will get aldehyde.

b) Secondary alcohols on oxidation we will get ketone.

c) In first step ester to weinreb amide which on further reaction with Grignard reagent we will get ketone.

d) Acid chloride on reaction with Gillmen reagent we will get ketone.