4.1 IUPAC Nomenclature of Alkanes and Cycloalkanes | Organic Chemistry

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Love your videos! I am preparing for Organic Chem 1 in the fall, any suggestions on what chapters I should watch/learn to get ahead?

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I would recommend mastering the fundamentals. That is isomers, resonance, hybridization, and Bronsted Acids/Bases. The most USEFUL thing you could do is get comfortable drawing bond-line/skeletal structures. Hope this helps.

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@@veronicajakubikova6875 No problem! Are you a pre-med student? Good luck self-teaching!

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[@ChadsPrep]

Sure did Ricky! But more than a bit ago. I'll take it as a compliment that I'm still recognizable! ;)

[@rickyl7442]

@@ChadsPrepWOW! The reason I asked this is I was talking to my cousin a former ASU grad about OChem since I just finished it also. He told me he would’ve failed also just like me if it wasn’t for his TA. I told him I would’ve also if it wasn’t for your videos. He asked the name of the person I watch and told him yours and showed him a video of yours. He said “no way that’s HIM!!”. You helped my cousin become a doctor and are helping me on my way to become one also. Hope you have a great day God bless. (Also you’re still very recognizable to him haha)

[@ChadsPrep]

That is fantastic Ricky! I can't tell you how much I miss working with students at ASU...still even live a few miles from campus. Best wishes on the journey and pass on my congratulations to your cousin! May God bless you in return!

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@@ChadsPrep thanks so much! Yeah I’m following in his footsteps by going to ASU and everything lol. You’re great have a great rest of your day!!

[@wowmanjaro]

So with saying "chlorocyclohexane" its understood that chloro is in the #1 carbon spot. For the second example can we not say "2-methyl chlorocyclohexane" since the chloro would have to be at the #1 spot? And so on "4-bromo-2-methyl chlorocyclohexane"? Thanks!!

[@wowmanjaro]

I typed "2-methyl-chlorocyclohexane" into some IUPAC programs and it successfully brought up the same structure.

[@ChadsPrep]

Hey Joshua! I saw 1 professor accept such a name over a decade ago so I decided to do a little digging before answering. Unfortunately, my digging wasn't very fruitful. I'll start by saying that many organic compounds go by multiple names. Some are historical and some are the IUPAC systematic names. And sometimes IUPAC adopts common historical names as being proper!! And sometimes there are even multiple acceptable IUPAC systematic names (substituted benzenes come to mind). But even when this is the case there is a "preferred IUPAC name" or PIN. 2-methyl-1-chlorocyclohexane is the PIN in this case and I had trouble finding a specific IUPAC rule for a disubstituted cycloalkane that would even identify if leaving out the 1 is acceptable. So not helpful here, sorry. The exception to this that you'll learn later is if 1 of the two substituents is named as part of the parent chain then it will be at position 1 by default and the #1 is omitted from the name. 2-methylcyclohexanol for instance. Since the alcohol is named as part of the parent chain it has the priority and on a cyclic structure would be at position #1 by default and so it is omitted from the name. Hope this helps at least a little! Happy Studying!

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I use "Missy Elliott Paints Beautiful Portraits, Her Husband Oscar Never Does" to remember the prefixes.

[@ChadsPrep]

Good job, Jedelande - Whatever works!

[@upleo-bj5dl]

Hi, could you help me explain how some subsitutants are called propan-2-yl or butan-2-yl?

[@ChadsPrep]

These are alternative ways to name complex substituents...and I haven't seen them used much. Propan-2-yl is the same thing as an isopropyl group (common name) or 1-methylethyl group (systematic name). The '2' in propan-2-yl indicates that this substituent is 3 carbon substituent but is attached to the rest of the molecule via the 2nd carbon. You'll see such names used more commonly with certain functional groups like esters for example. So you might have 1-methylethyl butanoate a.k.a. isopropyl butanoate but which could also be called propan-2-yl butanoate. Similarly, butan-2-yl is the same thing as sec-butyl (common name) or 1-methylpropyl. It is a 4-carbon substituent that is attached to the rest of the molecule via the 2nd carbon. Hope this helps!

[@upleo-bj5dl]

@@ChadsPrep Ah, that clears up everything. My teacher for the course (SCH4U - Ontario Grade 12 Chemistry) has mandated us to use the more IUPAC accurate name than the before IUPAC name. I've been stuck at this for a week but I couldn't stop thinking about this! Thank you - you are an amazing explainer

[@mup1537]

Why do we add the 1-chloro to 1-chloro-2methylcyclohexane? Why isn’t it just chloro like the example before?

[@ChadsPrep]

With only 1 substituent it would have to be at position 1. But with multiple substituents it gets confusing. But I did see one professor on one occasion over a decade ago allowing students to do exactly as you suggest. But I haven't seen it again. I actually invested some time earlier this year to answer this exact question. I looked up the IUPAC rules themselves (instead of a textbook's version of them) and couldn't find it addressed specifically, so I'm going to keep teaching it as presented in all the major textbooks with which I'm familiar. Happy studying!🙂

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@@ChadsPrep Thank you Chad. My gf had you as a TA so it's been very helpful using your videos in advance of taking the course where I am.

[@susantori6625]

12:43 instead of saying 3-ethyl-2-methylheptane, why can't it be 3-isopropylheptane? That seems easier

[@ChadsPrep]

Hey Susan! If you look up those 2 compounds they are actually different. 3-isopropylheptane has an isopropyl group at carbon 3 rather than an ethyl group and is missing the methyl group at C2. Hope that helps!

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