Question

1. Provide the products of the reaction below and a detailed reaction mechanism using curved arrows to indicate the movement of electrons. (a) (b) КОН (c) Note that formation of 4- or 7-membered rings is disfavored. Hiyo KOH acidie workup 2. An interesting problem that involves a bit of review (imines and Grignard chemistry) and application of what you previously learned to a new reaction: The Carbon of an imine functional group (i.e. R.C-NR) is sufficiently electron deficient to be attacked by Grignard reagents. After addition of aqueous acid during the workup, an amine is formed. With the help of this information, please predict products A and B and write down the detailed mechanism for each step for the following sequence: l-amino-propane reacts with cyclopentanone to give product A, after workup with weak acid. Product A then reacts with 1-butylmagnesium bromide, followed by treatment with weak acid to give product B. 3. Enamines, formed from ketones and secondary amines, are powerful nucleophiles at the second carbon (called the b carbon) away from the nitrogen, due to the resonance structure depicted below. This carbon can undergo standard SN2 reactions. The initial product has a positively charge nitrogen which is a resonance structure of the heteroatom- stabilized carbocation on the far right. That carbocation is usually reacted with water, which leads to formation of a ketone, exactly reversing the order of the steps in the enamine formation. nucleophilic carbon formed in several steps via With this information, provide the products for the reaction of the enamine shown above with 1-bromopropane followed by treatment with water and a detailed reaction mechanism using curved arrows to indicate the movement of electrons: do not skip steps.

Answer 1

For multiple question only first question is to be done, if nothing mentioned by you.
Solution ) OH Acidic (prodmet) mechanismo KOH Kt et on (base) Work (It is an example (Ритом ) of Aldol reaction) : - con le d OH e Bo o n (product)

mechi I-DY apr N lepy LN PT (DA) С им. veryone to Be (Product ). proton LDA is . from bulky base and more hindered abstract position. kol y acidic 4 (product) ® only mo hivyo ning world up : Korkta on Mein; OHO -Ngo I elimination -OH mople of product) intramolecular Aldo intramolecular condensation rxn. It is an example of
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