Question

Draw a structural formula for the product of the aldol reaction of each compound and for the \(\alpha, \beta\)-unsaturated aldehyde or ketone formed from dehydration of each aldol product. (a) CCC=O (b) CC(=O)c1ccccc1 (c) CC(=O)CCC(C)=O

Short answer

Question: Draw the structural formula for the product of the aldol reaction and the α, β-unsaturated aldehyde or ketone formed from dehydration of each aldol product for (a) Butanal, (b) Acetophenone, and (c) 4-Ketoheptane. Answer: (a) Butanal: Aldol product: CCCC(O)C(O)C Dehydration product: CCCC(O)C=C (b) Acetophenone: Aldol product: CC(O)c1ccccc1C(O)c2ccccc2 Dehydration product: CC(O)c1ccccc1C=Cc2ccccc2 (c) 4-Ketoheptane: Aldol product: CCCC(O)CCCCCC(O)C Dehydration product: CCCC(O)CCCCC=C(C)O

Step-by-step solution

Identify Enolizable Hydrogen and Enol Form

In butanal, the enolizable hydrogen is next to the carbonyl group (C=O). So, the enol form is: CC=C(O)C

Perform Aldol Reaction

The aldol reaction between two molecules of butanal, where the enolate ion of one molecule (enol form) attacks the carbonyl carbon of another molecule of butanal, gives us the aldol product. The aldol product in this case is: CCCC(O)C(O)C

Dehydration of Aldol Product

Next, we can dehydrate the aldol product to obtain the \(\alpha, \beta\)-unsaturated aldehyde. The dehydration product is: CCCC(O)C=C (b) CC(=O)c1ccccc1 - Acetophenone

Identify Enolizable Hydrogen and Enol Form

In acetophenone, the enolizable hydrogen is next to the carbonyl group (C=O). So, the enol form is: C=C(O)c1ccccc1

Perform Aldol Reaction

The aldol reaction between two molecules of acetophenone, where the enolate ion of one molecule (enol form) attacks the carbonyl carbon of another molecule of acetophenone, gives us the aldol product. The aldol product in this case is: CC(O)c1ccccc1C(O)c2ccccc2

Dehydration of Aldol Product

Next, we can dehydrate the aldol product to obtain the \(\alpha, \beta\)-unsaturated ketone. The dehydration product is: CC(O)c1ccccc1C=Cc2ccccc2 (c) CC(=O)CCC(C)=O - 4-Ketoheptane

Identify Enolizable Hydrogen and Enol Form

In 4-ketoheptane, the enolizable hydrogen is next to the carbonyl group (C=O). So, the enol form is: CCC=C(O)CC(C)=O

Perform Aldol Reaction

The aldol reaction between two molecules of 4-ketoheptane, where the enolate ion of one molecule (enol form) attacks the carbonyl carbon of another molecule of 4-ketoheptane, gives us the aldol product. The aldol product in this case is: CCCC(O)CCCCCC(O)C

Dehydration of Aldol Product

Next, we can dehydrate the aldol product to obtain the \(\alpha, \beta\)-unsaturated ketone. The dehydration product is: CCCC(O)CCCCC=C(C)O