Chapter 5: Problem 49
Terephthalic acid is obtained by the oxidation of ( \(\mathrm{X}\) ) with acidified \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{r^{*}}(\mathrm{X})\) is (a) ortho xylene (b) meta xylene (c) para xylene (d) ethylbenzene
Short Answer
Expert verified
Answer: (c) para xylene
Step by step solution
01
Write out the molecular structure for each choice.
We need to identify the molecular structure of each choice.
- Ortho xylene has two methyl groups substituted at the 1,2 positions on the benzene ring.
- Meta xylene has two methyl groups substituted at the 1,3 positions on the benzene ring.
- Para xylene has two methyl groups substituted at the 1,4 positions on the benzene ring.
- Ethylbenzene has an ethyl group substituted at the 1 position on the benzene ring.
02
Identify which compound can give terephthalic acid upon oxidation with acidified potassium dichromate.
Oxidation of xylene by acidified potassium dichromate essentially converts methyl groups (-CH3) to carboxyl groups (-COOH). The conversion happens at all the substitution locations.
- Ortho xylene oxidation would produce an isomer of phthalic acid with -COOH groups at 1,2 positions.
- Meta xylene oxidation would produce phthalic acid with -COOH groups at 1,3 positions.
- Para xylene oxidation would produce terephthalic acid with -COOH groups at the 1,4 positions.
- Ethylbenzene oxidation would produce benzoic acid with one -COOH group at the 1 position.
03
Find the correct choice.
We are looking for the compound that forms terephthalic acid upon oxidation with acidified K2Cr2O7. From our analysis in step 2, only para xylene forms terephthalic acid upon oxidation. Therefore, the correct answer is:
(c) para xylene
Unlock Step-by-Step Solutions & Ace Your Exams!
-
Full Textbook Solutions
Get detailed explanations and key concepts
-
Unlimited Al creation
Al flashcards, explanations, exams and more...
-
Ads-free access
To over 500 millions flashcards
-
Money-back guarantee
We refund you if you fail your exam.
Over 30 million students worldwide already upgrade their learning with Vaia!
Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Organic Chemistry
Organic chemistry is a branch of chemistry that involves studying the structure, properties, composition, reactions, and preparation of carbon-containing compounds, which include not only hydrocarbons but also compounds with any number of other elements, including hydrogen, nitrogen, oxygen, halogens, phosphorus, silicon, and sulfur. This field of chemistry is fundamental when understanding complex molecules such as pharmaceuticals, plastics, and organic materials found in everyday life.
The process of identifying the structures of organic compounds and predicting their reactivity involves understanding various functional groups and how they behave under different conditions. In the scenario of terephthalic acid synthesis, recognizing the relationship between the starting material, which is a benzene derivative, and the product of an oxidation reaction is crucial in organic synthesis. The exercise provided sheds light on how understanding the molecular structure of organic compounds affects the outcome of chemical reactions.
The process of identifying the structures of organic compounds and predicting their reactivity involves understanding various functional groups and how they behave under different conditions. In the scenario of terephthalic acid synthesis, recognizing the relationship between the starting material, which is a benzene derivative, and the product of an oxidation reaction is crucial in organic synthesis. The exercise provided sheds light on how understanding the molecular structure of organic compounds affects the outcome of chemical reactions.
Oxidation Reactions
In organic chemistry, oxidation reactions involve the loss of electrons by a molecule, atom, or ion. However, in a more practical sense, it often refers to the increase in the oxygen content of a compound or the decrease in hydrogen content.
Oxidizing Agents
Compounds such as potassium dichromate (\( \text{K}_2\text{Cr}_2\text{O}_7 \) in an acidified medium is a potent oxidizing agent used to transform various functional groups. The strength and selectivity of the oxidizing agent are critical factors in determining the products of oxidation reactions.Mechanisms of Oxidation
In the case of benzenes, the methyl groups attached to the ring are susceptible to oxidation. Specifically, in an oxidation reaction with acidified potassium dichromate, the methyl group (\text{-CH}_3) is converted to a carboxyl group (\text{-COOH}). This conversion is a vital step in synthesizing compounds like terephthalic acid, where accurately identifying the position of the substituents on a benzene ring can lead to the prediction of the product structure.Benzene Derivatives
Benzene derivatives form an essential class of organic molecules where substituents replace one or more hydrogen atoms in the benzene ring. These derivatives form the basis for many compounds used in industry and medicine.
For example, in the exercise about terephthalic acid synthesis, the knowledge of where the methyl groups are located on the xylene molecule (ortho, meta, or para) directly determines the type of phthalic acid formed upon oxidation. Thus, understanding how various substituent patterns behave under chemical reactions is key to predicting the outcomes in organic synthesis, rather than merely memorizing facts.
Substitution Patterns
The position of the substituents on a benzene ring significantly influences the chemical properties and reactivity of the derivative. Common positional labels are ortho (1,2-), meta (1,3-), and para (1,4-) for disubstituted benzene derivatives. Each configuration has unique properties and reactivity patterns.For example, in the exercise about terephthalic acid synthesis, the knowledge of where the methyl groups are located on the xylene molecule (ortho, meta, or para) directly determines the type of phthalic acid formed upon oxidation. Thus, understanding how various substituent patterns behave under chemical reactions is key to predicting the outcomes in organic synthesis, rather than merely memorizing facts.