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Chapter 5: Problem 159

Which of the following compounds will give methyl vinyl ketone by aldol condensation followed by dehydration? (a) Formaldehyde and acetaldehyde (b) Formaldehyde and acetone (c) Acetaldehyde and acetone (d) Two molecules of acetaldehyde

Short Answer

Expert verified
Answer: (b) Formaldehyde and Acetone.

Step by step solution

01

Understand Aldol Condensation and Dehydration reaction

Aldol condensation is an organic reaction in which an enolate ion reacts with an aldehyde or ketone to form a β-hydroxy aldehyde or β-hydroxy ketone. This reaction is then followed by dehydration, in which a molecule of water is removed, leading to the formation of an α,β-unsaturated aldehyde or ketone.
02

Write out the structures of the given compounds

We need to identify the structures for the given compounds: (a) Formaldehyde: H-CHO Acetaldehyde: CH3-CHO (b) Formaldehyde: H-CHO Acetone: CH3-CO-CH3 (c) Acetaldehyde: CH3-CHO Acetone: CH3-CO-CH3 (d) Two molecules of Acetaldehyde: CH3-CHO
03

Perform Aldol Condensation

Perform the aldol condensation reaction on each of the pairs and determine the resulting β-hydroxy aldehyde or β-hydroxy ketone product for each pair: (a) Formaldehyde (H-CHO) and Acetaldehyde (CH3-CHO) give CH3-CH(OH)-CH2-CHO (b) Formaldehyde (H-CHO) and Acetone (CH3-CO-CH3) give H-CH(OH)-CH2-CO-CH3 (c) Acetaldehyde (CH3-CHO) and Acetone (CH3-CO-CH3) give CH3-CH(OH)-CH2-CO-CH3 (d) Two molecules of Acetaldehyde(CH3-CHO) give CH3-CH(OH)-CH2-CHO
04

Perform Dehydration

Perform a dehydration reaction on each of the products obtained from step 3: (a) CH3-CH(OH)-CH2-CHO gives CH3-CH=CH-CHO (b) H-CH(OH)-CH2-CO-CH3 gives H-CH=CH-CO-CH3 (Methyl vinyl ketone) (c) CH3-CH(OH)-CH2-CO-CH3 gives CH3-CH=CH-CO-CH3 (d) CH3-CH(OH)-CH2-CHO gives CH3-CH=CH-CHO
05

Compare the products to Methyl Vinyl Ketone

Compare the products from step 4 to Methyl Vinyl Ketone (H-CH=CH-CO-CH3): (a) CH3-CH=CH-CHO is not equal to Methyl Vinyl Ketone (H-CH=CH-CO-CH3) (b) H-CH=CH-CO-CH3 is equal to Methyl Vinyl Ketone (H-CH=CH-CO-CH3) (c) CH3-CH=CH-CO-CH3 is not equal to Methyl Vinyl Ketone (H-CH=CH-CO-CH3) (d) CH3-CH=CH-CHO is not equal to Methyl Vinyl Ketone (H-CH=CH-CO-CH3) Hence, the correct answer is (b) Formaldehyde and Acetone.

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Most popular questions from this chapter

The reagent that can be used for the conversion of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCHO}\) to \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH}\) is (a) Alkaline \(\mathrm{KMnO}_{4}\) (b) \(\mathrm{Zn}(\mathrm{Hg}) / \mathrm{HCl}\) (c) \(\mathrm{PCC} / \mathrm{CH}_{2} \mathrm{Cl}_{2}\) (d) Tollens' reagent

The IUPAC name of is CCC(C=O)CC(C)C (a) 2 -ethyl-4-methylpentanal (b) 4 -methyl 2 -ethylpentanal (c) 2 -methylhexanal (d) 2 -ethylhexanal

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCl}+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Cd} \rightarrow\) product \((\mathrm{s})\). The major organic product obtained is (a) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

When acetone reacts with chloroform in the presence of alkali like \(\mathrm{NaOH}\), the product formed is (a) Chloropionium (b) acetic acid (c) Chloretone (d) mesityloxide

O=C1C=CCCC1 O=C1CCCCC1 (ii) \(\mathrm{H}_{3} \mathrm{O}^{+} /\). O=C1C=CCCC1=C1CCCCC1 (i)(X) The reagent (X) required is (a) \(\mathrm{NaOH}\) (b) \(\mathrm{I}_{2} / \mathrm{NaOH}\) (c) KCN (d) \(\mathrm{CF}_{3} \mathrm{CO}_{3} \mathrm{H}\)
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