Unveiling Nitriles and Isonitriles: The Chemical Journey

Entering the Discovery Portal

Chemical Curiosity: Did you know that nitriles are commonly used in the production of medications and that isocyanides are explored in the synthesis of new materials? That's right! These organic functions hold tremendous importance in modern chemistry, and their applications are as vast as they are fascinating. Let's dive into this chemical world and explore their structures and nomenclature.

Quizz: Can we identify and correctly name the nitriles and isocyanides present in our daily lives and in the pharmaceutical industry?

Exploring the Surface

Organic functions play a crucial role in organic chemistry, and two of these functions, nitriles and isonitriles, are particularly important due to their diverse and impactful applications. But before we delve deeper, let's establish a solid foundation to understand these structures. Nitriles, also known as cyanides, consist of a cyano group (-CN) attached to a hydrocarbon. And isonitriles, or isocyanides, have the general formula R-NC, where the nitrogen atom is directly linked to the terminal carbon of the chain.

The importance of these compounds extends across various industries. In pharmaceutical sciences, nitriles are essential in the synthesis of many medications, serving as crucial intermediates. Isonitriles, while less common, are explored in the creation of advanced materials due to their unique chemical properties. Furthermore, the ability to correctly name and identify these compounds is fundamental not only for theoretical understanding but also for practical application in research and the development of new products.

Now, let's explore how IUPAC, the International Union of Pure and Applied Chemistry, defines the rules and guidelines for naming nitriles and isonitriles. Knowing these rules not only facilitates communication among chemists but also ensures precision in the description of chemical structures. Throughout this chapter, we will discuss these standards in detail and learn fun and interactive techniques to master the nomenclature of these compounds. Get ready for an engaging and enlightening chemical dive!

What Are Nitriles?

Alright, everyone! Let's start with the basics: nitriles, these wonders of organic chemistry. Imagine a carbon group with a triple bond to a nitrogen atom - sounds like the beginning of a joke, right? But no, it's a nitrile! Ah, how exciting!  Found in various compounds, they are recognized by that famous cyano group (-CN). Kind of like, if chemistry were a soap opera, nitriles would be the characters with a crucial role in the main plot, but who sometimes go unnoticed amidst all the drama.

Now, if you're thinking this is all too complicated, relax and breathe. Nitriles, once known as cyanides (you know, the poison from old movies? Kind of like that, but in a less deadly way), are compounds that show up in useful things like solvents, plastics, and believe it or not, even in medications! Yes, that medicine your grandma takes might have a nitrile as a supporting actor for her health! 

Think of nitriles as the hipsters of organic chemistry - always in the know, useful, and a little misunderstood. They are key players in many important chemical reactions, especially in organic syntheses (translating from chemese: they are really good at helping create new chemical compounds). So if someone asks you today 'what is a nitrile?', you can confidently reply: 'it's an awesome compound that has this amazing cyano group and pops up in the most unexpected places!'

Proposed Activity: Online Cyano Hunt

Go to the class forum and post a picture of a compound with a cyano group that you found on the internet. Mark where you got the image from and describe in your own words what is interesting about the compound! Then, like and comment on your classmates' posts (with compliments, of course!). 

Nomenclature of Nitriles - The Rules of the Game

Okay, let's have a chat about the naming rules for nitriles. Imagine we're playing a game where 'nailing the nomenclature' is the passport to the next level of organic chemistry. According to IUPAC (the mega supreme authority on chemical names), a nitrile is named by adding 'nitrile' to the end of the corresponding hydrocarbon name. For example, methane becomes methanenitrile. You might be thinking: 'Seriously? That's it?' Yes, folks, easy peasy! It sounds like child's play!

But don’t get too excited, not everything is sunshine and rainbows. When you have a more complex chain, like one with several branches and substituents (those fancy words to say that the compound has some 'hang-ons'), then things heat up! The cyano group is always the boss, so we count from it. If the molecule has a fork at carbon number 3, we name it considering that the carbon of the cyano is the most important. Example? Hexan-3-nitrile, just so you know I'm not all talk! 

Guys, I know chemistry sometimes feels like a weird sci-fi movie, but believe me, with practice, the nomenclature rules become second nature. Let's simplify even more: think of the rules like assembling a puzzle. You have all the pieces; you just need to know how to fit them together. And so you don’t feel lost, how about practicing a bit right now with an interactive activity?

Proposed Activity: Naming Like a Pro

Create a list of five simple compounds and name each of them as if they were a nitrile, following IUPAC rules. Post your list in the class WhatsApp group. Then, positively critique your classmates' lists, pointing out any mistakes or congratulating them when everything is correct.

Isonitriles - The Unique Cousins

Now that you’re practically a Jedi master of nitriles, it's time to meet their unique cousins: isonitriles.  If nitriles are the goody-two-shoes of the group, isonitriles are the rebels without a cause, but with an impressive scientific utility. Instead of a cyano group, isonitriles have an NC- group (nitrogen-carbon, in that order!).

You may be thinking: 'So what?' Well, my friends, this inversion changes everything! Isonitriles have unique chemical properties and are highly investigated in advanced organic synthesis. Although they aren't as common as nitriles, they hold a special place in the hearts of many chemists for their applications in advanced materials and even in the synthesis of new medications.

So, picture yourself at a scientific party where each molecule is trying to stand out. Isonitriles show up charmingly, showing they are different, and that ends up being a plus in many sophisticated chemical reactions. Think we’re exaggerating? Then get ready to discover this for yourself with a super cool interactive activity! 

Proposed Activity: Uncle Internet Hunt

Using your phone, search for a scientific article or news about the application of isonitriles, take a screenshot, and post it in the class forum. Add a comment about what you found most interesting or surprising about the use of these isonitriles. Don't forget to check and comment on your classmates' posts too!

The Difference that Makes a Difference

Alright, folks! Now that we know what nitriles and isonitriles are and how to name them, it's time to point out the main differences between these two types of compounds. It's like two siblings - one is the proud icon of the family, and the other is the rebel, but both have their unique qualities!

First, that basic difference: the functional group. Nitriles have the general formula R-CN, where the triple-bonded carbon is directly linked to nitrogen. Meanwhile, in isonitriles, we are talking about R-NC, with the nitrogen coming first like the leader of the rock band! This changes quite a bit their reactivity and applications. Nitriles are pretty common in the industry and in everyday things. Isonitriles, however, are smarter, showing up in specific niches of research and development!

Second, we need to highlight the chemistry itself. Due to structural differences, these compounds have distinct properties and, of course, particular chemical reactions. Nitriles are more stable under various conditions, while isonitriles love a little chaos, being more reactive and used in more complicated chemical syntheses. In other words, understanding these differences is essential to avoid confusing the roles of each in a chemical reaction or practical application! 

Proposed Activity: Mission: Comparison

Draw (or find) a chemical structure containing nitriles and another one with isonitriles and post them in the WhatsApp group. Write below each one the main differences you identified between them. The interaction doesn’t stop there - comment on the other students' posts telling them if they are correct or what they could improve! 

Creative Studio

In chemical formulas we started to explore, With nitriles and isonitriles, we dug deep, and more. The cyano group, with its firm triple bond shining bright, And the rebellious NC, proclaiming its properties outright.

Meticulous nitriles, prospering in the industry, In plastics and pharmaceuticals, always collaborating, you see. Unique isonitriles, innovating new reactions, In advanced science, playing a unique role in transactions.

IUPAC rules we learned, without hesitation, Methane becomes methanenitrile, a new way of creation. Counting carbons, always from the cyano's face, In this chemical game, knowledge we trace.

Distinguishing these compounds, an essential task indeed, We studied their structures, every special detail we need. Stable or reactive, they know how to shine, In organic chemistry, a chapter that is divine.

Reflections

• How do the chemical properties of nitriles influence their broad industrial application?
• Why is correct nomenclature crucial for scientific communication in chemistry?
• What are the crucial differences in reactive behavior between nitriles and isonitriles, and how does this affect their practical applications?
• How can understanding these organic functions impact the development of new materials and medications?
• In what ways can we apply the approach of digital and interactive technologies to other topics in chemistry to make learning more engaging?

Your Turn...

Reflection Journal

Write and share with your class three of your own reflections on the topic.

Systematize

Create a mind map on the topic studied and share it with your class.

Conclusion

 Engaging Conclusion: We have reached the end of this vibrant chapter about nitriles and isonitriles! We saw that, despite their structural differences, both play crucial roles in organic chemistry and have fascinating applications in industry and research.  From the making of medications to new technological materials, these substances demonstrate how dynamic and powerful organic chemistry can be.

 Next Steps: For our next active class, keep reviewing the concepts of naming and structure of nitriles and isonitriles. Use the proposed exercises, interact with your classmates in digital activities, and go further: seek more practical examples of these organic functions around you. The more you practice and discuss, the better prepared you will be to lead discussions in the classroom and carry out the proposed projects with mastery. Get ready to dive even deeper and have fun discovering how chemistry is present in our daily lives! 