
Concept explainers
(a)
Interpretation: The product of Perkin condensation has to be written
Concept introduction: For the given condensation reactions,
In first case, acetic anhydride is treated with a base and a proton is abstracted. The enolate ion thus formed attacks carbonyl carbon of benzaldehyde. Loss of water molecule results in the formation of the product of Perkin condensation.
In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.
In third case, diethyl malonate is treated with a base and enolate ion is formed. Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species. Loss of a water molecule results in the formation of the product of Knoevenagel reaction.
In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives
(b)
Interpretation: The compound formed after addition of water to the product of Perkin condensation has to be written.
Concept introduction: For the given condensation reactions,
In first case, acetic anhydride is treated with a base and a proton is abstracted. The enolate ion thus formed attacks carbonyl carbon of benzaldehyde. Loss of water molecule results in the formation of the product of Perkin condensation.
In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.
In third case, diethyl malonate is treated with a base and enolate ion is formed. Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species. Loss of a water molecule results in the formation of the product of Knoevenagel reaction.
In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.
(c)
Interpretation: The product of Knoevenagal condensation has to be written
Concept introduction: For the given condensation reactions,
In first case, acetic anhydride is treated with a base and a proton is abstracted. The enolate ion thus formed attacks carbonyl carbon of benzaldehyde. Loss of water molecule results in the formation of the product of Perkin condensation.
In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.
In third case, diethyl malonate is treated with a base and enolate ion is formed. Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species. Loss of a water molecule results in the formation of the product of Knoevenagel reaction.
In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.
(d)
Interpretation: A compound formed after product of Perkin condensation is heated in an acidic medium has to be written
Concept introduction: For the given condensation reactions,
In first case, acetic anhydride is treated with a base and a proton is abstracted. The enolate ion thus formed attacks carbonyl carbon of benzaldehyde. Loss of water molecule results in the formation of the product of Perkin condensation.
In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.
In third case, diethyl malonate is treated with a base and enolate ion is formed. Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species. Loss of a water molecule results in the formation of the product of Knoevenagel reaction.
In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.

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Chapter 18 Solutions
Organic Chemistry
- Select the stronger base from each pair of compounds. (a) H₂CNH₂ or EtzN (b) CI or NH2 NH2 (c) .Q or EtzN (d) or (e) N or (f) H or Harrow_forward4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HOarrow_forwardb. H3C CH3 H3O+ ✓ H OHarrow_forward
- 2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3arrow_forwardIdentify and provide an explanation that distinguishes a qualitative and quantitative chemical analysis. Provide examples.arrow_forwardIdentify and provide an explanation of the operational principles behind a Atomic Absorption Spectrometer (AAS). List the steps involved.arrow_forward
- Instructions: Complete the questions in the space provided. Show all your work 1. You are trying to determine the rate law expression for a reaction that you are completing at 25°C. You measure the initial reaction rate and the starting concentrations of the reactions for 4 trials. BrO³¯ (aq) + 5Br¯ (aq) + 6H* (aq) → 3Br₂ (l) + 3H2O (l) Initial rate Trial [BrO3] [H*] [Br] (mol/L) (mol/L) | (mol/L) (mol/L.s) 1 0.10 0.10 0.10 8.0 2 0.20 0.10 0.10 16 3 0.10 0.20 0.10 16 4 0.10 0.10 0.20 32 a. Based on the above data what is the rate law expression? b. Solve for the value of k (make sure to include proper units) 2. The proposed reaction mechanism is as follows: i. ii. BrО¸¯ (aq) + H+ (aq) → HBrO3 (aq) HBrO³ (aq) + H* (aq) → H₂BrO3* (aq) iii. H₂BrO³* (aq) + Br¯ (aq) → Br₂O₂ (aq) + H2O (l) [Fast] [Medium] [Slow] iv. Br₂O₂ (aq) + 4H*(aq) + 4Br(aq) → 3Br₂ (l) + H2O (l) [Fast] Evaluate the validity of this proposed reaction. Justify your answer.arrow_forwardе. Д CH3 D*, D20arrow_forwardC. NaOMe, Br Brarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning

