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Ch. 14 - Synthetic TechniquesWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation

Organometals aren't the only way to create new carbon-carbon bonds. It turns out we can use a sodium alkynide (nucleophile) as well to react with alkyl halides and other electrophiles to form a new C-C bond as well. 

Concept #1: Sodium Alkynide Alkylation


Part of the synthetic cheat sheet taught you guys how to make carbon-carbon bonds and that's what I want to focus on in this topic. I really just want to destroy the entire concept of organometals and sodium alkynide alkylation.
Basically, you guys know, this is the only way to make carbon-carbon bonds in orgo one is through organometals. Strong sodium alkynides are really commonly used organometals and because they happen to be strong nucleophiles. What that means is that since they're strong nucleophiles, they're often paired or reacted with alkyl halides because those are strong electrophiles.
What we can do is we can get a negative on a carbon to be attracted to a positive on a carbon and bam. You have a new carbon-carbon bond, which is very important because synthesis relies on making bigger molecules from smaller ones. So if you can add carbons, that's really important.
But for these, for sodium alkynides, we're not going to just need to know that it's a nucleophile and attacks an electrophile. We're going to need to know a few more things. How to generate the alkynide. That means alkynide synthesis, making it from scratch. We need to know how to do that. Also, after you've done your reaction, you also need to know how to transform the triple bond afterwards, so there's a lot to know here. We need to know how to make the alkynide. Then how to use it and then how to lose it, how to do different things to it.
Once again, I had this graphic that showed different nucleophiles. The ones that we're going to be dealing with are mostly on this page because I want you guys to get special practice with these are the alkynides and the alkyl halides.
So what we're going to do first is we're going to start from kind of ascending hardness. We're going to start with the easiest problem. It's not easy, but it's not that bad and we're going to work our way to progressively harder and harder problems, where I'm going to take you further and further back in the synthetic process and you're going to have to figure out everything from the very beginning.
But in this case, like I'm telling you right now, this is not such a bad question. Let me coach you through it and see if you can get it. Because notice that right now – first of all, I'm already starting with a triple bond. That's awesome because if you're going to notice, I have three carbons in this molecule. I have four carbons in the other.
What does that mean that must have happened at some point? If I added carbon, if you added carbon that means you must have used an organometal. Like I said, the most common organometal in this chapter is going to be sodium alkynide. I already have a triple bond, so that's a huge giveaway that I just need to use that triple bond.
Basically, what you should be thinking is how many carbons do I need to add to the triple bond to make four and then what do I need to do to that triple bond afterwards so it looks like a double bond. It looks like that. That was enough hint. I'm just trying to coach you guys so this isn't totally like a train wreck. I'm going to stop the video and you guys try to answer it the best that you can. 

Once we create these triple bond nucleophiles and use them in our synthesis, we will will also learn how to get rid of them and transform them to double bonds (cis and trans) and single bonds.


Let's get to work. These will be multi-step transformations. Do your best to see if you can fill in the correct reagents! 

Practice: Propose a synthesis:

Practice: Propose a synthesis: