Chapter 1: Problem 31
The IUPAC name of \(\mathrm{CH}_{3}-\mathrm{CO}-\mathrm{CHCl}-\mathrm{CH}_{2}-\mathrm{COOH}\) is (a) 3-Chloro-4-oxopentanoic acid (b) 4-Oxo-3-Chloropentanoic acid (c) 2-Oxo-3-Chloropentanoic acid (d) 1 -Carboxy-3-Chloro-4-ketobutane
Short Answer
Expert verified
a) 2-Chloro-3-oxopentanoic acid
b) 3-Oxo-2-chloropentanoic acid
c) 2-Oxo-3-chloropentanoic acid
d) 3-Chloro-2-oxopentanoic acid
Answer: c) 2-Oxo-3-chloropentanoic acid
Step by step solution
01
Identify the longest carbon chain
The longest carbon chain in the given compound consists of 5 carbon atoms: \(\mathrm{CH}_{3}-\mathrm{CO}-\mathrm{CHCl}-\mathrm{CH}_{2}-\mathrm{COOH}\). So, the parent name of the compound will be based on "pentane".
02
Identify the primary functional group
The primary functional group is a carboxylic acid group (-COOH) present at the end of the carbon chain. Hence, the suffix for the compound will be '-oic acid', resulting in 'pentanoic acid'.
03
Assign locants to substituents
We have two substituents in the compound: a chlorine atom (Cl) and a carbonyl group (C=O). The carbonyl group is present on the second carbon atom, and the chlorine atom is present on the third carbon atom. Therefore, the locants assigned to these substituents are 2 and 3, respectively.
04
Name substituents in alphabetical order
The substituents are the chlorine atom (chloro-) and the carbonyl group (oxo-). In alphabetical order, we list them as chloro- and then oxo-.
05
Combine the elements of the IUPAC name
Combining the parent name, the primary functional group, and the substituents with their assigned locants in alphabetical order, we arrive at the IUPAC name: 3-Chloro-2-oxopentanoic acid. Therefore, the correct answer is (c) 2-Oxo-3-Chloropentanoic acid.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Organic Compounds Nomenclature
Understanding the nomenclature of organic compounds is crucial as it provides a consistent way of naming chemical compounds so that scientists can communicate unambiguously. In organic chemistry, names are constructed based on the structure of the molecule and follow rules established by the International Union of Pure and Applied Chemistry (IUPAC). The IUPAC naming involves several key steps:
- Identification of the longest continuous carbon chain (the parent hydrocarbon).
- Determination of the primary functional group, which influences the suffix of the name.
- Numeration of the carbon atoms in the chain (locants) starting from the end nearest a functional group.
- Naming of substituents (groups attached to the main chain) and prefixing them to the parent name in alphabetical order.
Functional Groups in Organic Chemistry
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They are like 'functional badges' that dictate how a molecule will behave in chemical reactions. In organic chemistry, these groups include hydroxyl (-OH), carbonyl (C=O), carboxyl (-COOH), amino (-NH2), and many others.
Let's use the example from the exercise solution to illustrate functional groups in context. The given compound has two functional groups: a carbonyl group and a carboxylic acid group. Identifying and understanding these groups helped the student derive the correct IUPAC name. Each functional group has a specific priority that influences its position and the compound's overall name, which brings us to the concept of priority in the nomenclature.
Let's use the example from the exercise solution to illustrate functional groups in context. The given compound has two functional groups: a carbonyl group and a carboxylic acid group. Identifying and understanding these groups helped the student derive the correct IUPAC name. Each functional group has a specific priority that influences its position and the compound's overall name, which brings us to the concept of priority in the nomenclature.
Priority of Functional Groups
In the IUPAC system, functional groups have a hierarchical priority that determines which groups take precedence in nomenclature. The priority is based on the reactivity and presence of these groups. For instance, carboxylic acids hold the highest priority among common functional groups, followed by anhydrides, esters, amides, and so forth.
In the textbook exercise, the student perceived that the carboxylic acid group had higher priority over the carbonyl group. This understanding is vital because it influenced the naming, ensuring the '-oic acid' suffix was used, reflecting the highest priority functional group in the compound.
In the textbook exercise, the student perceived that the carboxylic acid group had higher priority over the carbonyl group. This understanding is vital because it influenced the naming, ensuring the '-oic acid' suffix was used, reflecting the highest priority functional group in the compound.
Locants in Chemical Compounds
Locants are numerical prefixes that denote the position of a substituent or functional group on the main carbon chain in an organic compound. They are assigned starting from the end of the carbon chain nearest to the functional group with the highest priority, minimizing the numbers associated with each substituent. It's important to note that the locants must lead to the lowest set of numbers for all substituents when there are choices.
Returning to our exercise, the student correctly assigned the locants by starting numbering from the end of the chain closest to the carboxylic acid. This led to the functional groups being assigned locants '2' for the oxo (carbonyl) group and '3' for the chloro (chlorine) substituent. This step is fundamental as incorrect locants can result in a completely different and incorrect name for the compound.
Returning to our exercise, the student correctly assigned the locants by starting numbering from the end of the chain closest to the carboxylic acid. This led to the functional groups being assigned locants '2' for the oxo (carbonyl) group and '3' for the chloro (chlorine) substituent. This step is fundamental as incorrect locants can result in a completely different and incorrect name for the compound.