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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 17, Problem 3b

Name the following:
b. Chemical structure of a nitrile with a carbonyl group, featuring a hexagonal ring and a cyano group attached.

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1
Step 1: Identify the parent chain. The structure is a cyclic compound with seven carbon atoms, making it a cycloheptane ring.
Step 2: Determine the functional groups present. The molecule contains a ketone group (C=O) and a nitrile group (-C≡N).
Step 3: Assign priority to the functional groups based on IUPAC nomenclature rules. The ketone group has higher priority than the nitrile group, so the ketone will determine the base name and numbering.
Step 4: Number the ring starting from the carbon of the ketone group as position 1, and proceed in the direction that gives the nitrile group the lowest possible number.
Step 5: Combine the name of the parent chain, the position of the substituents, and the functional groups to form the complete name. The methyl group is at position 3, and the nitrile group is at position 6.

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Key Concepts

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

Nitriles

Nitriles are organic compounds that contain a cyano group (-C≡N), where a carbon atom is triple-bonded to a nitrogen atom. They are typically derived from carboxylic acids by replacing the -OH group with a -CN group. Nitriles are important in organic synthesis and can be converted into various functional groups, including amines and carboxylic acids.
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IUPAC Naming Conventions

The International Union of Pure and Applied Chemistry (IUPAC) provides systematic rules for naming organic compounds. This includes identifying the longest carbon chain, determining the functional groups present, and assigning locants to indicate the position of substituents. Understanding these conventions is essential for accurately naming complex organic structures.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and nitrile (-C≡N). Recognizing functional groups is crucial for predicting the behavior of organic compounds and for proper nomenclature.
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