Chapter 1: Problem 158
The correct IUPAC name of \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}\) is (a) \(1,3,5\) -Trioxabutane (b) \(2,4,6\) -Trioxabutane (c) \(2,4,6\) -Trioxaheptane (d) Dimethoxydimethyl ether
Short Answer
Expert verified
(a) 1,3,5-Trioxabutane
(b) 2,4,6-Trioxabutane
(c) 2,4,6-Trioxaheptane
(d) Dimethoxydimethyl ether
Answer: (d) Dimethoxydimethyl ether
Step by step solution
01
Identify the main chain
In the given compound \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}\), there are three carbon atoms in the main chain. Hence, the base name of the compound should be derived from the base name of a three-carbon alkane, which is "propane".
02
Identify the oxygen-containing substituents
There are three oxygen-containing substituents in the given compound. Two of them are methoxy groups (\(\mathrm{OCH}_{3}\)) and one of them is an ethoxy group (\(\mathrm{OCH}_{2}\mathrm{OCH}_{3}\)). We should number the carbon atoms in the main chain in such a way that the substituents have the lowest possible numbers.
03
Number the carbon atoms and name the substituents
To give the lowest possible numbers to the substituents, we should number the carbon atoms as follows: \(\mathrm{1CH}_{3}-\mathrm{O}-\mathrm{2CH}_{2}-\mathrm{O}-\mathrm{3CH}_{2}-\mathrm{O}-\mathrm{4CH}_{3}\). In this case, the methoxy groups are at positions 1 and 4, the ethoxy group is at position 3.
04
Combine the substituents with the main chain
From the previous steps, we can now construct the IUPAC name of the given compound: \(\mathrm{1,4}\)-dimethoxy-\(\mathrm{3}\)-ethoxypropane.
Now let's compare our result with the given options:
(a) \(1,3,5\)-Trioxabutane
(b) \(2,4,6\)-Trioxabutane
(c) \(2,4,6\)-Trioxaheptane
(d) Dimethoxydimethyl ether
None of the given options matches with the IUPAC name we found. But option (d) "Dimethoxydimethyl ether" is the closest to our result because it also consists of two methoxy groups and one ethoxy group connected to a propane chain. Although it's not the IUPAC name we derived, it still describes the same compound.
Therefore, the correct answer is (d) Dimethoxydimethyl ether.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Nomenclature of Organic Compounds
Understanding the nomenclature of organic compounds is essential for students as it provides a systematic way of naming complex molecules. This system of naming is standardized by IUPAC (International Union of Pure and Applied Chemistry) and is universally accepted.
The nomenclature process begins by identifying the longest carbon chain in the molecule, which forms the 'base name' of the compound. The presence of functional groups and substituents are then noted, and prefixes or suffixes are added to the base name to account for these. Numbers are used to indicate the position of the substituents on the main chain.
For the above compound, the longest chain is a three-carbon alkane, and the base name is derived from 'propane'. Multi-functional groups like ethers in the exercise are addressed as substituents, in this case as a 'methoxy' and an 'ethoxy' group. The position is then numbered to give the lowest numbers to the substituents, leading to the name '1,4-dimethoxy-3-ethoxypropane'.
While the exercise's solution identified by the student doesn't match the multiple-choice options, understanding the process is crucial for students preparing for competitive exams like IIT JEE, where the correct IUPAC names are frequently tested.
The nomenclature process begins by identifying the longest carbon chain in the molecule, which forms the 'base name' of the compound. The presence of functional groups and substituents are then noted, and prefixes or suffixes are added to the base name to account for these. Numbers are used to indicate the position of the substituents on the main chain.
For the above compound, the longest chain is a three-carbon alkane, and the base name is derived from 'propane'. Multi-functional groups like ethers in the exercise are addressed as substituents, in this case as a 'methoxy' and an 'ethoxy' group. The position is then numbered to give the lowest numbers to the substituents, leading to the name '1,4-dimethoxy-3-ethoxypropane'.
While the exercise's solution identified by the student doesn't match the multiple-choice options, understanding the process is crucial for students preparing for competitive exams like IIT JEE, where the correct IUPAC names are frequently tested.
Organic Functional Groups
Organic functional groups are specific groupings of atoms within molecules that have their own characteristic properties. They are responsible for the unique chemical behavior of those molecules. Some common functional groups include alcohols, carboxylic acids, ethers, amines, and alkenes.
In the provided exercise, the functional groups at play are the 'ether' groups represented by oxygen atoms connecting alkyl chains. Specifically, 'methoxy' and 'ethoxy' groups are present. Recognizing these groups is crucial because it dictates how the rest of the molecule is constructed.
The naming of ethers is slightly more complex than other functional groups. When multiple ether groups are present as substituents, they are not named as a separate functional group but are named as alkoxy substituents, reflecting their attachment to the main chain.Learning to identify and name these groups accurately is fundamental for students, especially when dealing with more advanced topics in Organic Chemistry.
In the provided exercise, the functional groups at play are the 'ether' groups represented by oxygen atoms connecting alkyl chains. Specifically, 'methoxy' and 'ethoxy' groups are present. Recognizing these groups is crucial because it dictates how the rest of the molecule is constructed.
The naming of ethers is slightly more complex than other functional groups. When multiple ether groups are present as substituents, they are not named as a separate functional group but are named as alkoxy substituents, reflecting their attachment to the main chain.Learning to identify and name these groups accurately is fundamental for students, especially when dealing with more advanced topics in Organic Chemistry.
Organic Chemistry IIT JEE
Organic Chemistry comprises a significant part of the syllabus for the Indian Institute of Technology Joint Entrance Examination (IIT JEE), one of the most competitive engineering entrance exams in India. Students must master organic chemical reactions, mechanisms, and the nomenclature of organic compounds.
Solving problems like the one discussed exemplifies the level of understanding required for IIT JEE. It is not just about memorizing the rules but also being able to apply them to unfamiliar compounds.
For IIT JEE, it's crucial for students to be thorough with IUPAC nomenclature standards, grasp the characteristics of various organic functional groups, and apply this knowledge in a time-bound examination environment. The correct interpretation and naming of the compounds, including complex scenarios as seen in the exercise, are consistent types of questions seen in the examination.
The ability to deduce the correct structural name despite not matching the given options demonstrates the analytical skills needed to excel in Organic Chemistry for IIT JEE.
Solving problems like the one discussed exemplifies the level of understanding required for IIT JEE. It is not just about memorizing the rules but also being able to apply them to unfamiliar compounds.
For IIT JEE, it's crucial for students to be thorough with IUPAC nomenclature standards, grasp the characteristics of various organic functional groups, and apply this knowledge in a time-bound examination environment. The correct interpretation and naming of the compounds, including complex scenarios as seen in the exercise, are consistent types of questions seen in the examination.
The ability to deduce the correct structural name despite not matching the given options demonstrates the analytical skills needed to excel in Organic Chemistry for IIT JEE.