Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Problem 35a

Chapter 17, Problem 35a

The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
a.

Verified step by step guidance

Step 1: Identify the amino acid structure shown in the image. The compound has an amino group (-NH2), a carboxylate group (-COO⁻), and a side chain containing an isopropyl group. This structure corresponds to leucine, an α-amino acid.

Step 2: Recall the Strecker synthesis method for amino acids. This method involves the reaction of an aldehyde with ammonia (NH3) and hydrogen cyanide (HCN) to form an α-aminonitrile, which is then hydrolyzed to yield the amino acid.

Step 3: Determine the aldehyde required for the synthesis of leucine. The side chain of leucine (isopropyl group) suggests that the aldehyde should be isobutyraldehyde (CH3CH(CH3)CHO). This aldehyde provides the correct carbon skeleton for leucine.

Step 4: Write the reaction sequence. In the Strecker synthesis, isobutyraldehyde reacts with ammonia and hydrogen cyanide to form an α-aminonitrile intermediate. This intermediate is then hydrolyzed under acidic conditions to produce leucine.

Step 5: Summarize the process. To synthesize leucine, the carbonyl compound is isobutyraldehyde. This compound undergoes the Strecker synthesis pathway to yield the desired amino acid.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Amino Acids

Amino acids are organic compounds that serve as the building blocks of proteins. They contain both an amino group (-NH2) and a carboxylic acid group (-COOH), making them α-aminocarboxylic acids. The structure of amino acids allows them to participate in various biochemical reactions, including the formation of peptide bonds, which link them together to form proteins.

Reductive Amination

Reductive amination is a chemical reaction that involves the conversion of a carbonyl compound (such as an aldehyde or ketone) into an amine. This process typically involves the formation of an imine intermediate, which is then reduced to yield the amine. In the context of amino acid synthesis, this reaction is crucial for introducing the amino group into the carbon skeleton derived from the carbonyl compound.

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbonyl group (C=O), which can be found in aldehydes, ketones, carboxylic acids, and esters. In the synthesis of amino acids, specific carbonyl compounds are selected based on their ability to react with amines through reductive amination, ultimately leading to the formation of the desired amino acid structure.

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Textbook Question

Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?

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Textbook Question

Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.

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Textbook Question

What are the products of the following reactions? (A trace amount of acid is present in each case.)

a. cyclopentanone + ethylamine

b. cyclopentanone + diethylamine

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Textbook Question

Imines can exist as stereoisomers. The isomers are named using the E,Z system of nomenclature (Section 4.2 ). The lone pair has the lowest priority.

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Draw the structure of each of the following compounds:

a. the (E)-hydrazone of benzaldehyde

b. the (Z)-oxime of propiophenone

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Textbook Question

Which ketone forms the most hydrate in an aqueous solution?

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Textbook Question

The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?

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The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?a.

Verified video answer for a similar problem:

Key Concepts

Amino Acids

Reductive Amination

Carbonyl Compounds

The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
a.