Alkanes and Cycloalkanes: The Basics

Now that we have our Gen Chem fundamentals down, we journey into the land of Alkanes, our first true taste of Organic Chemsity. This series, albeit not what I consider to be the most fun part of OChem, is where we learn to name molecules (with common names and IUPAC nomenclature), how molecules orient themselves in space and how that affects their internal energy, and our very first reaction & mechanism: free radical halogenation. So buckle up--the organic party is truly about to get started.

Study Guide(s):

Worksheet(s) & Solution(s):

Videos:

  1. Fun with Functional Groups--an Overview

    https://joechem.io/videos/9 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at a bunch of different functional groups you'll encounter in your organic chemistry career. Again, there is a bit of annoying memorization here, but I guarantee two things: One, on your first test, learning these will earn you some easy points. Two, if you don't commit these to memory now, you'll get tripped on little things later down the line when we start doing real organic chemistry and reactions WITH these various functional groups. So bear down a bit, learn them now and make some new organic friends.

  2. Intro to Alkanes & Some Physical Properties

    https://joechem.io/videos/10 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, before we dive deeper into the world of alkanes, we'll have a brief alkane introduction: what they are, a summary of their physical properties, and much more. I like to have a bit of overview and talk about physical properties for each functional group before getting hot and heavy with their reactions (I think in most cases physical properties can help explain some of the behavior we see in various situations in Ochem).

  3. Determining How Substituted Carbons Are

    https://joechem.io/videos/203 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll dive into how to answer the question of 'how substituted is this particular carbon?'. We'll go over how to identify methyl, primary, secondary, tertiary, and quaternary carbons as well as explore how to apply that terminology to situations where carbons are attached to functional groups.

  4. Determining How Substituted Double Bonds Are

    https://joechem.io/videos/204 for video on jOeCHEM. In this video, we'll dive into how to answer the question of 'how substituted is this particular double bond?'. We'll go over how to identify mono, di, tri, and tetra substituted double bonds and discuss how being more or less substituted affects a double bond's stability.

  5. Using Cis/Trans versus E/Z to Describe Double Bonds

    https://joechem.io/videos/205 for video on jOeCHEM. In this video, we'll clear the air as to when you can use cis/trans, E/Z, or neither when describing a double bond. What you'll see is that cis/trans terminology works in specific situations, and E/Z is more generally and can always be used. However, we'll see how both can be utilized with tons of examples.

  6. Common Naming of Organic Compounds

    https://joechem.io/videos/11 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we talk about Common Naming and the little bit of "slang" you'll need in the Organic world. Although this is a little bit of annoying memorization, but put the work in to nail these various names down: They will pop up time and time again, and its an expectation by people in the Organic world that if someone says "t-butyl alcohol" you know exactly what they're talking about.

  7. IUPAC/Systematic Naming

    https://joechem.io/videos/12 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll get hands on with IUPAC Systematic Naming of organic structures. Although we have Common Naming down, and we can talk the talk a bit, we need to be savvy with how the IUPAC outlines naming for organic molecules (since you can't name EVERYTHING with common naming). Again, this is one of those slightly less exciting topics in Ochem, but get this process down and it's an easy chance for you to pick up points on an exam.

  8. IUPAC Naming with Other Functional Groups

    https://joechem.io/videos/101 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we build on what we learned in our first systematic naming video (https://joechem.io/videos/12), tackling IUPAC naming with molecules that contain multiple functional groups of different varieties.

  9. Newman Projection State of Mind

    https://joechem.io/videos/13 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we introduce the Newman Project--a new way for us to look at molecules. In doing so, we'll discuss different types of molecular strain, such as torsional and steric and how we can graphically draw a molecule's internal energy as its bonds rotate.

  10. Cyclohexane: Up Close and Personal

    https://joechem.io/videos/14 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we meet our new, very stable friend cyclohexane. We'll talk about why cyclohexane is extremely stable and the different conformations cyclohexane takes on (chairs and boats specifically). Finally, we'll talk about how to find the most stable/unstable conformations when substituents are added to a cyclohexane ring.

  11. Free Radical Halogenation - Part 1 - The Mechanism

    https://joechem.io/videos/15 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we are introduced to what is most commonly the first real organic reaction taught in organic chemistry classes: Free Radical Halogenation. The overview of this reaction is that we can take any old, plain alkane (such as ethane) and replace a C-H bond with a C-X bond--removing a Hydrogen and sticking on a halogen (such as Br or Cl) in its place. We'll walk through this whole reaction, step by step, through what is called the reaction mechanism. During the mechanism, we'll use curved arrows to show how electrons move and facilitate the various steps of the reaction.

  12. Free Radical Halogenation - Part 2 and Hyperconjugation

    https://joechem.io/videos/16 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we continue to talk about the Free Radical Chain Rxn. Having gone through the mechanism already (https://joechem.io/videos/15), this video serves to unravel the mystery of why Free Radical Chlorination is less selective (or "picky", if you will) as opposed to Bromination. Well, it all can be explained by the inner workings of the reaction mechanism combined with a concept called Hyperconjugation, and thats what we dive into in this video.

  13. Hammonds Postulate and Identifying Early or Late Transition States

    https://joechem.io/videos/114 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we pick apart what Hammond's Postulate is and how we can apply it to Energy Diagrams to determine whether a reaction had a "late" or "early" transition state.