Ch. 1 - A Review of General ChemistryWorksheetSee 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

Hydrocarbons fall into two categories: Saturated and Unsaturated- and both of these terms describe the number of hydrogens that carbon is bonded to. 

Definition of Saturation

Concept #1: The difference between saturated and unsaturated molecules.

Transcript

Hey, guys, so now we're going to talk about a topic called index of hydrogen deficiency and this is a topic that usually isn't covered in the first chapter of most textbooks. So, you're probably thinking, “Johnny, why are you teaching this to me if I don't need to know it yet?” Well, because there's this other topic called constitutional isomers and that topic is much easier to understand if you already know the IHD rules.
So what I'm going to do here is I'm going to jump a little bit forward and teach you something that you don't need to know yet because it's going to make isomers so much easier to understand for this chapter. Let's go ahead and begin.
There's actually two different ways to compute the IHD and that is one structural and the other one is with molecular formula. What I'm going to do on this page is just show you the structural one which is actually the easier one and then we'll move on to molecular formula.
First of all, let's just talk about what is index of hydrogen deficiency. Well, what it has to do with is how unsaturated or saturated a molecule is. So what's that word saturated? Well, a saturated molecule is any molecule that has as many hydrogens as possible.
And there's this formula that we can use in all chemistry to figure out if it has as many hydrogens as possible. And that formula is – maybe you remember it from gen chem – it's 2n plus 2, where n is equal to the number of carbons.
So I have my 2n plus 2 rule. What that's going to do is it's going to predict for me how many hydrogens I need for my structure for it to be fully saturated, meaning that it has as many hydrogens as it can possibly hold. Any molecule that has less than that number, 2n plus 2, is going to be considered to be unsaturated.
These are words, saturated and unsaturated, they might sound familiar to you. That's because these are words we use actually in cooking. Saturated fat would actually be a fat – fats are these long carbon chains – it would be this fat that has as many hydrogens as possible. An unsaturated fat would be one that's missing a few hydrogens.
So you might be wondering, “Okay, Johnny, what makes carbons miss hydrogens? Why would you be missing some?” It turns out it only happens for two different reasons. I'm going to write this down. It happens for pi bonds. Remember that pi bonds just have to do with double bonds or triple bonds. They both have pi bonds. Then also, rings.
Rings are also going to take away some of the hydrogens from a molecule because what that means is that one of the ends is supposed to be CH3 and the other end is supposed to be CH3, but when you make a ring, they have to fuse together so that means that now you have to make them CH2's. What I'm trying to say is that a ring actually takes some hydrogens away from the carbon structure. 
 

The equation 2n + 2 (where n = #carbons) predicts the number of hydrogens that an organic molecule should contain to be considered saturated.

  • If the total number of hydrogens < 2n + 2, then the molecule is unsaturated. 

Are the following molecules saturated?

Hint: You can figure this out without using the 2n + 2 rule.  

Example #1: Is the following molecule saturated? Is it missing any hydrogens? How many if so?

Transcript

So if we use 2n plus 2, n in this case equals 5. So I'll do 2 times 5 plus 2 and that would mean that I need to have 12 hydrogens in order to be fully saturated. So then I would go ahead and ask myself does this have 12 hydrogens. And if you count what you would find is that would have 1, 2, 3, 4, 5, 6, 7, 8, 9 10, 11, 12. Wow! Look at that. I actually do have 12 hydrogens.
So that means that is this molecule saturated or unsaturated? This would be saturated.
That's the first thing, so now I just showed you a molecule that's saturated. Now another way that you could have know that this 2qs saturated, besides doing the formula, is you could have also asked yourself, okay, what makes things unsaturated? Well, pi bonds and rings. Did this chain have any pi bonds in it? No. It's all single bonds. Did it have any rings? No.
So also by looking at that, you could have said, “Oh, this is going to be a saturated molecule.” See, that's how this gets really easy. 

Example #2: Is the following molecule saturated? Is it missing any hydrogens? How many if so?

Transcript

And it turns out that this one would be 2 times 6 plus 2, so we should have 14 hydrogens. But how many does it actually have? That's right, 12. I know you counted everyone, each one has 2. So this one actually has 12 hydrogens. Is it missing any hydrogens? Yes, it's actually missing two hydrogens.
Okay, does that make sense? So this would be considered unsaturated. 

Example #3: Is the following molecule saturated? Is it missing any hydrogens? How many if so?

Transcript

So this was also the same formula, 2 times 6 plus 2. It should have 14 H's. But how many does it actually have? Well if you think about bondline structure, there's only supposed to be 1 H in each of these positions, meaning that I only have 6 H's, meaning that I'm actually missing how many? I'm missing 8 H's. That's huge.
In the first one, I had all the H's possible. In the second one, I'm missing 2 and in the third one, I'm missing 8. 

Predicting IHD Structurally

*IHD is also known as the Degree of Unsaturation.

Concept #2: What index of hydrogen deficiency is.

Transcript

So we know that we can use the words saturated and unsaturated to describe this, but is there a way to compare these guys? So is there a way to say, okay, which one is more unsaturated and which one is less unsaturated because they're both very different. The answer is yes. What we do is we use the IHD rules to really be very explicit about which one is the most unsaturated and which one is the least.
So the way that we do this is really easy. All we do is say that one IHD is the equivalent of missing two hydrogens. So if you're missing two hydrogens, that would be the equivalent of one index of hydrogen deficiency. That's just like the conversion.
The way that this works is that a ring or a double bond is going to count as one IHD, one IHD. And then a triple bond is going to count as two IHD because if you think about it a triple bond has two pi bonds in it so that would be two IHD.
And really that is it. Now instead of having to use that complicated formula – I mean the formula isn't hard, but it's just a little tedious sometimes. Imagine if you had like 11 carbons or something and you're having to maybe use more times tables then just your fingers or whatever. What I'm trying to say is that it can get tedious counting all those hydrogens out, so instead we use these rules. 

Basically the IHD is an easy way for us to compare how unsaturated a molecule is compared to another.

  • 1 IHD = Compound is missing 2 hydrogens.
  • Rings/Double bonds = 1 IHD  
  • Triple Bonds = 2 IHD

What is the IHD of the following molecules?

Example #4: What is the IHD of the following molecule? 

Example #5: What is the IHD of the following molecule? 

Example #6: What is the IHD of the following molecule? 

Predicting IHD using Molecular Formula

Unfortunately, the structure of a compound will not always be drawn for us. In that case, we use the following technique.

Concept #3: How to use IHD with molecular formula.  

Transcript

When you're given a molecular formula to calculate IHD, you don't have the same clues that you had let's say if it was a structure. If you remember, we could use pi bonds or rings to figure out how many hydrogens were missing from a molecule. But when you're just given a molecular formula, let's say like, this example, C4H7Cl, I have no clue if there's rings there, if there's double bonds there. Really, all I have is the atoms.
So for this, we're going to have to use our own rule and our own formula because that's really the only way to solve it. Now your professor may have used a different rule in class, and in fact, most of the rules that I've seen are different from mine. The only reason I've settled on this one is because it worked for a lot of my students and they like it better. But if you have a rule that your professor taught you that you like better, please, by all means, use that one.
But this is the way it works, basically we need to calculate IHD and the way we do that is by calculating the theoretical H's. The way we do that is by using the formula 2n plus 2. So basically we calculate 2n plus 2. Then we subtract the actual number of hydrogens. But the thing is that for this we don't just use hydrogens, we also take into consideration other atoms that might act as hydrogen equivalents.
For example, when I'm calculating the number of hydrogens in a molecule, I don't just look at H, I also look at X's. Do you guys remember what X is? X would be a halogen and that counts as one hydrogen. For this formula, I count a halogen and a hydrogen exactly the same.
Then oxygen, what about if I see an oxygen in my compound? What do I could that as? Actually, I count that as zero. I ignore it. Whenever you see oxygen in this compound, just ignore it. That doesn't go into your equation.
Then how about nitrogen? Nitrogen is a special case. Nitrogen is actually going to count as negative one hydrogen for the overall compound. So that means that I'm not just counting H's, I'm also counting all halogens and all nitrogens and I'm ignoring the oxygens.
Finally, I get that number. That number is going to go here. This is going to be number of H's total. Then I'm going to take that number and I'm going to divide it all by 2, which is what I have here and that's going to be your IHD.
Now I know that sounds a little bit complicated, but once you get going with it, you can actually do it pretty fast.

*If your professor taught you a different method, that’s fine! Whatever helps you get the right answer. 

Example #7: What is the IHD for C4H7Cl?  

Example #8: What is the IHD for C6H7N?  

Example #9: What is the IHD for C7H12O2?  

Awesome job. Now we know how to easily calculate and compare the number of hydrogens that are missing for all types of compounds. 

Additional Problems
Determine the index of hydrogen deficiency (degrees of unsaturation) for the following molecule  Cancer, a tyrosine kinase inhibitor - Bosutinib  
Determine the molecular formula corresponding to the following structure. Calculate the number of degrees of unsaturation from the molecular formula and evaluate whether your calculations agree with the structure shown.  
A certain hydrocarbon has a molecular formula of C5H8 . Which of the following is not a structural possibility for this hydrocarbon? (a) It is a cycloalkane. (b) It contains one ring and one double bond. (c) It contains two double bonds and no rings.  (d) It is an alkyne. 
Determine the molecular formula corresponding to the following structure. Calculate the number of degrees of unsaturation from the molecular formula and evaluate whether your calculations agree with the structure shown.  
Based on the trends above, answer the following questions about the structure of a compound with molecular formula C24H48. Is it possible for this compound to have a triple bond? Is it possible for this compound to have a double bond?
Calculate the IHD, index of hydrogen deficiency, for a compound of molecular formula C5H9O2Br.
Calculate the degree of unsaturation for C6H10S.
What is the  unsaturation number of limonene? A. 0 B. 1 C. 2 D. 3 E. 4 F. 5 G. 6 H. 7 I. 8 J. 9
What is the index of hydrogen deficiency of each of the following molecules?
An acyclic alkane has 20 hydrogen atoms. How many carbon atoms are present in this molecule? (A molecule is acyclic if its structure contains no rings.)   A. 6                       B. 7                      C. 8                          D. 9                       E. 10 F. 11                     G. 12                    H. 13                         I. 14                     J. None of these
Which of the following compounds have the same degree of unsaturation? a.I &amp; II b.I &amp; III c.III &amp; IV d.II &amp; III e.I &amp; IV
Determine the degree of unsaturation of the following formulas.
Calculate the IHD, index of hydrogen deficiency, for a compound of molecular formula C12H18N3F2ClNO3.
How many degrees of unsaturation does the following compound have? A)        4 B)        5 C)        6 D)        7  E)       8
What is the index of hydrogen deficiency of each? (Hint: Think about their MF's)
In each pair below, circle the compound with the largest index of hydrogen deficiency; circle both if the index of hydrogen deficiency is the same.
Expand the following structural representations so as to more clearly show all the atoms and any unshared electron pairs. What are their molecular formulas? Are any of them isomers? 
Expand the following structural representations so as to more clearly show all the atoms and any unshared electron pairs. What are their molecular formulas? Are any of them isomers? 
Expand the following structural representations so as to more clearly show all the atoms and any unshared electron pairs. What are their molecular formulas? Are any of them isomers?
Expand the following structural representations so as to more clearly show all the atoms and any unshared electron pairs. What are their molecular formulas? Are any of them isomers?
Are there any cyclic alkenes with the molecular formula C 41H82?
What can be said about the structure of the carbon skeleton of an aldehyde or ketone with molecular formula C14H28O?
The general molecular formula for alkanes is  CnH2n+2. What is the general molecular formula for:(d) Cyclic hydrocarbons that contain one double bond 
For the following formula, C7H10NBr, calculate the IHD and select all the types of unsaturation that might be present in the molecule based on the IHD. 
Are there any nitriles with molecular formula C50H101N?
Are there any cyclic ethers with molecular formula C48H98O?
Are there any cyclic alkenes with molecular formula C41H82?
Alkane (A) has a molecular formula of C11H20. How many rings are present in alkane (A)?
Alkane (B) has a molecular formula of C14H18. How many rings are present in alkane (B)?
Can a molecule with the molecule formula C34H70O be a ketone? Could it be an alcohol? Could it be an ether? Why or why not?
The degree of unsaturation, or index of hydrogen deficiency, is the number of pi bonds plus rings in a molecule.Specify the degree of unsaturation (index of hydrogen deficiency) of the following formulas:(a) C26H28(b) C11H14(c) C8H4Br3N(d) C19H20(e) C6H10O3(f) C9H12N2(g) C7H8(h) C8H8O3(i) C10H8N2
Determine the index of hydrogen deficiency (degrees of unsaturation) for the following molecule.Antipsychotic - Haloperidol = C21H23NO2ClF
How many unsaturations are present in the following compound?A. noneB. 2C. 3D. 5E. 6
A compound with the formula C5H8 can be either an alkene or an alkyne.a. Trueb. False 
Which of the following molecules have a Hydrogen Deficiency Index of 2? Select all of the molecules that apply.
Which of the above sections of this molecule would be considered a saturated portion of the molecule? 
The index of hydrogen deficiency for C7H6Br4O2 is 3. Select one: a. True b. False 
An organic compound, pictured below, has the chemical formula C 7H10Cl2. How many degrees of unsaturation are present?a. 1b. 2c. 3d. 4