HOAldol reactions (condensation of two aldehydes or ketones to yield a ẞ-hydroxy carbonyl) can go inreverse (ẞ-hydroxy carbonyl to two aldehyde/ketones, a retro-aldol). Propose mechanisms for thefollowing two transformations, using both intra-molecular aldol and a retro-aldol reactions. Be sureto follow the rules we have discussed for writing reaction mechanisms!Na OEtethanolOHO

The mechanism of the following transformation will be -

Answered: HO Aldol reactions (condensation of two…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 56AP

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Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?
Propose a mechanism to account for the formation of 3, 5-dimethyl- pyrazole from hydrazine and 2, 4-pentanedione. Look carefully to see what has happened to each carbonyl carbon in going from starting material to product.
The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde toform an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)
Propose a suitable synthetic route to carry out the following transformations
The enolate derived from diethyl malonate reacts with a variety of electrophiles (not just alkyl halides) to form new carbon–carbon bonds. With this in mind, draw the products formed when Na+ −CH(CO2Et)2 reacts with each electrophile, followed by treatment with H2O.
) Cinnamaldehyde is used in artificial cinnamon flavoring. Show how cinnamaldehydeis synthesized by a crossed aldol condensation followed by dehydration.H CHcinnamaldehyde C COH(b) Adding acetophenone slowly to a cold solution of LDA produces the enolate of acetophenone; but adding LDA slowly to a cold solution of acetophenone produces acondensation product. Show the reactions happening in each case, and explain why weobserve such different results
Provide a mechanism for the following transformation
1. Discuss the role of the Aldol condensation reaction in the synthesis below. What specific reaction was used in the synthesis? What is the importance of the aldol reaction in the entire synthetic approach? 2. Show the detailed reaction mechanism involved in their corresponding specific parts in this syntheses.
What product would you expect from aldol cyclization of hexanediol in basic solution?
The Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-keto ester and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product: Draw the β-keto ester as an ethyl ester,
The Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-diketone and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product:
many useful synthetic produces involve sequences of adol, Claisen, Michael, and Mannich reactions. Write the mechanism for each transformation.

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