Chapter 15: Problem 21
Draw structures corresponding to the following IUPAC names: (a) cis-Cyclohexane-1,2-dicarboxylic acid (b) Heptanedioic acid (c) Hex-2-en-4-ynoic acid (d) 4-Ethyl-2-propyloctanoic acid (e) 3-Chlorophthalic acid (f) Triphenylacetic acid (g) Cyclobut-2-enecarbonitrile (h) \(m\) -Benzovlbenzonitrile
Short Answer
Step by step solution
Understanding Names and Identifying Functional Groups
Constructing Basic Structures
Positioning Functional Groups
Applying Stereochemistry
Finalizing the Structures with Substituents and Unsaturations
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
IUPAC Naming
To name an organic molecule, follow these steps:
- Identify the longest carbon chain in the compound. This becomes the parent name, such as 'hexane' for a six-carbon chain.
- Number the chain from the end nearest a substituent or functional group to give the lowest numbers possible in the name.
- Identify and name the substituents or functional groups attached to the main chain. Substituents are named in alphabetical order, with their position numbers prefixed to them.
- Combine these parts together into a single name, using appropriate locants and prefixes to indicate positions and multiplicity of identical groups.
- Final check: Ensure the name adheres to IUPAC's standard conventions and includes all necessary positional indicators.
Functional Groups in Organic Chemistry
Some key functional groups you'll encounter include:
- Hydroxyl (-OH): Found in alcohols.
- Carboxyl (-COOH): Found in carboxylic acids like heptanedioic acid.
- Aldehyde (-CHO): Found in compounds like hexanal.
- Keto (C=O): Found in ketones, such as acetone.
Understanding and identifying these functional groups allow chemists to predict the behavior and reactions of organic compounds. It's also a key aspect when drawing molecules based on IUPAC names, as seen in the exercise examples.
Stereochemistry
Terms often used in stereochemistry include:
- Cis and Trans: Describes the orientation of functional groups in a molecule relative to a plane of symmetry, often in cyclic structures or alkenes. In "cis-cyclohexane-1,2-dicarboxylic acid," the carboxylic acid groups are on the same side of the cyclohexane ring plane.
- Chirality: Chiral molecules are those that cannot be superimposed on their mirror image, like left and right hands. This can lead to isomers with different biological activities or properties.
- Enantiomers and Diastereomers: Types of stereoisomers where enantiomers are mirror images and diastereomers are not.
For instance, when drawing the structure of a molecule from its IUPAC name, knowing if something is 'cis' or 'trans' helps accurately depict the actual three-dimensional form of the molecule.