### Protection of Aldehydes and Ketones as Acetals and Ketals Aldehydes and ketones can be "protected" as acetals and ketals. Complete the following outlined reactions, showing how the protection is accomplished, and what results after deprotection.1. **Starting material:** A benzene ring with a bromomethyl (—CH₂Br) substituent and an aldehyde (—CHO) group attached directly to the ring.2. **Formation of Acetal:** - The carbonyl group (aldehyde) reacts with a diol (ethylene glycol, C₂H₄(OH)₂) to form a cyclic acetal (with an oxygens in a five-membered ring). - This reaction effectively "protects" the carbonyl group by transforming it into an acetal, which is more stable under basic conditions and prevents it from undergoing unwanted side reactions.3. **Grignard Reaction:** - The bromo substituent reacts with magnesium (Mg) to form a Grignard reagent (R—MgBr), where R is the benzene ring attached to the oxygens of the acetal.4. **Reaction with Aldehyde/Ketone:** - The Grignard reagent reacts with a carbonyl compound (another aldehyde or ketone group) leading to the formation of a new carbon-carbon bond. 5. **Deprotection:** - The cyclic acetal is then hydrolyzed (broken down) back to the original carbonyl group using aqueous acid (H₃O⁺), completing the deprotection step, revealing the original functional group.### Diagram Explanation- The initial chemical structure consists of a benzene ring with a bromomethyl and an aldehyde group.- The aldehyde is protected by forming a cyclic acetal with ethylene glycol.- The bromine is replaced by a Grignard reagent (MgBr).- The Grignard reagent reacts with a new carbonyl compound to form an intermediate.- Finally, the cyclic acetal is hydrolyzed to restore the aldehyde group, completing the deprotection.Complete the reactions to show the final product after deprotection, illustrating the transformation and the utility of protection groups in synthetic organic chemistry.

Aldehydes and ketones are protected as acetals and ketals when treated with alcohols in the presence…

4. Aldehydes and ketones can be "protected" as acetals and ketals. Complete the following outlined reactions, showing how the protection is accomplished, and what results after deprotection. Br „MgBr 1) Br 2) H3O* deprotection here

4. Aldehydes and ketones can be "protected" as acetals and ketals. Complete the following outlined reactions, showing how the protection is accomplished, and what results after deprotection. Br „MgBr 1) Br 2) H3O* deprotection here

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

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Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

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An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

### Protection of Aldehydes and Ketones as Acetals and Ketals

Aldehydes and ketones can be "protected" as acetals and ketals. Complete the following outlined reactions, showing how the protection is accomplished, and what results after deprotection.

1. **Starting material:** A benzene ring with a bromomethyl (—CH₂Br) substituent and an aldehyde (—CHO) group attached directly to the ring.

2. **Formation of Acetal:**
- The carbonyl group (aldehyde) reacts with a diol (ethylene glycol, C₂H₄(OH)₂) to form a cyclic acetal (with an oxygens in a five-membered ring).
- This reaction effectively "protects" the carbonyl group by transforming it into an acetal, which is more stable under basic conditions and prevents it from undergoing unwanted side reactions.

3. **Grignard Reaction:**
- The bromo substituent reacts with magnesium (Mg) to form a Grignard reagent (R—MgBr), where R is the benzene ring attached to the oxygens of the acetal.

4. **Reaction with Aldehyde/Ketone:**
- The Grignard reagent reacts with a carbonyl compound (another aldehyde or ketone group) leading to the formation of a new carbon-carbon bond.

5. **Deprotection:**
- The cyclic acetal is then hydrolyzed (broken down) back to the original carbonyl group using aqueous acid (H₃O⁺), completing the deprotection step, revealing the original functional group.

### Diagram Explanation
- The initial chemical structure consists of a benzene ring with a bromomethyl and an aldehyde group.
- The aldehyde is protected by forming a cyclic acetal with ethylene glycol.
- The bromine is replaced by a Grignard reagent (MgBr).
- The Grignard reagent reacts with a new carbonyl compound to form an intermediate.
- Finally, the cyclic acetal is hydrolyzed to restore the aldehyde group, completing the deprotection.

Complete the reactions to show the final product after deprotection, illustrating the transformation and the utility of protection groups in synthetic organic chemistry.

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