(a)
Interpretation:
The product formed on aldol addition of phenylacetaldehyde is to be stated.
Concept introduction:
In aldol condensation reaction, the base abstracts an acidic proton from the
(b)
Interpretation:
The product formed on aldol addition of propionaldehyde is to be stated.
Concept introduction:
In aldol condensation reaction, the base abstracts an acidic proton from the
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EBK ORGANIC CHEMISTRY
- Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst. The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.arrow_forwardA "condensation" reaction involves the loss of a small neutral molecule as a follow-up step to an addition reaction. The product is an a,ß-unsaturated aldehyde (or ketone). (*In aldol condensations, the small neutral molecule is water.) Which of the three products shown is the correct aldol condensation products of the reaction shown. Write the mechanism for the dehydration step. Assume the reaction mixture still contains catalytic base. OH NaOH H O adol addition = enolates + aldehyde loty Condensation H or OH or H (H₂O + OH)arrow_forward4) Give an example of an enol which would tautomerize into a) an aldehyde and b) a ketone.arrow_forward
- 2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardExplain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis: (a) (CH3CCH;COOH; (b) C,H;CH2COOH; (c) (CHa)CCOOH.arrow_forwardPredict the product formed in the nucleophilic aromatic substitution reaction between 1-chloro-2,4-dinitrobenzene and sodium methoxide (NaOCH3). Draw the mechanism for the reaction, showing why the product you have selected is formed.arrow_forward
- Propose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forwardAcetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-.arrow_forwardDraw the synthons and synthetic equivalents for the following compounds. a) c) Meo b) d) O,N `NO2arrow_forward
- How to synthesize trans-2-methylcyclohexanol from cyclohexanone?arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Write the mechanism for each of the two reactions.arrow_forwardPlease draw out the mechanism for the reaction that involves the deprotonation of the acidic hydrogen on the ester followed by nucleophilic attack on the carbonyl carbon to form an enolate intermediate.arrow_forward