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Structural Isomers – Just How Many Structures Can You Make from a Simple Formula?

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Structural Isomers – Just How Many Structures Can You Make from a Simple Formula? 1 Lecture 6 Structural Isomers – Just how many structures can you make from a simple formula? 1. methane: CH4 2D formula 3D formula condensed formula H H CH4 H C H C H H methane H H 2. ethane: C2H6 Once the two carbons are connected, there are only six additional bonding sites and these are filled by the six hydrogen atoms. Ethane is a saturated molecule. C2H6 is completely unambiguous. 3D formula condensed formula 2D formula H H H H H C2H6 C C condensed line formula H C C H H H H H H CH3CH3 You can twist about this single bond generating ethane different conformations. Build a model and try it. The carbon-carbon single bond allows rotation of one group of three C-H sigma bonds past the other group of three C-H sigma bonds. Using a molecular model of ethane, fix one carbon with one hand and spin the other carbon with you other hand. The different arrangements of the atoms as they rotate past one another are called conformations. Conformations are the result of differences in a structure from rotation about single bonds. We will study conformations more in a later topic. R H R H In this drawing the bonds R H H H on the front carbon are C C rotated by 60o relative to R bonds on the back carbon. R H R R H R R The three front bonds can rotate around H the carbon-carbon single bond, like spokes H on a wheel or propeller blades on an airplane. = rear carbon atom = front carbon atom A straight-on view shows the three bonds as lines connecting to the front carbon atom, written as a small dot. The rear carbon is usually drawn as a large circle and the three bonds to that carbon are also drawn as lines, but only down to the circle. Rotation of the front bonds is easily seen in two different structures. These are called Newman projections and we will see more of them later. 3. propane: C3H8 Once again, there is only one possible arrangement of the bonding atoms. The third carbon has to be attached to either of the other two carbons forming a three carbon chain with eight additional bonding sites, each bonded to a hydrogen atom. Propane is a saturated molecule. C3H8 is completely unambiguous. 2 Lecture 6 condensed formula 2D formula 3D formula H H H H H H H C C C3H8 H C H C C H C C C H Because the backbone of the condensed line formula H C H carbon skeleton (plus the two H H H hydrogen atoms at the end H H positions) go up and down, CH3CH2CH3 propane You can twist about either single this shape is sometimes referred bond generating different to as a zig-zag shape. It can conformations. Build a model also be called a wedge and dash formula. and try it. Because single bonds allow rotation, there are a number of ways that propane can be drawn using slightly different representations. If you have models, now is a time to use them. Keep them handy. You’ll want to use them frequently. H This bond was H This bond was H H twisted down. H H twisted down. H H H H C C H H H H H H C C C H H C C H H C C H H C C H H C C H H H H H H H H H C C H This bond was H H This bond was H H twisted up. twisted up. H H The point you should get from this example is that three sequentially attached sp3 carbon atoms can be drawn in a variety of ways, but are still the same structure. With additional carbon atoms (4, 5, 6…) the possibilities increase, but the feature to focus on when deciding if two structures are identical or different is the length of the carbon chain and the length and positions of its branches. Whether you have 3,4,5, or more carbon atoms zig-zagged in any manner possible, you can always redraw it in a simpler straight chain form. The straight chain representation is easier for you to work with, so choose it as your method of drawing a 2D structure (even if it is changing its shape thousands of times per second). Drawing your structures with a straight chain, as much as possible, will give you the best chance of not overlooking a structure. We will use this approach in our subsequent examples. 4. butane and 2-methylpropane (isobutane): C4H10 We finally encounter an example where there is more than one possible carbon skeleton. First draw the longest possible carbon chain, which would be...four carbons (you guessed it!). There are ten additional bonding sites that are all saturated with hydrogen atoms. C4H10 is ambiguous. condensed formula 2D formula 3D formula (ambiguous) H H H H H H H H C4H10 Rotation is possible about H C C C C H H C C any of the carbon-carbon condensed line formula C C H single bonds, generating CH CH CH CH different conformations. 3 2 2 3 H H H H Build a model and try it. H H butane H H 3 Lecture 6 A four carbon chain can be drawn and rotated in a variety of ways, but there is no change effected in the skeletal connectivity of the atoms. No matter how the bonds are twisted, it’s still a four carbon chain. C C C C C C C C C C C C C C C C C C C C Let’s now shorten our chain by one carbon atom so that the longest chain is three carbon atoms. Can we attach our remaining carbon atom in such a way so as to not make a four carbon chain. By attaching the fourth carbon atom to the middle carbon of our three carbon chain, the longest chain is only three carbon atoms in any direction, and we have a one carbon atom branch in the middle. This is a different carbon skeleton, and it has a different name: 2-methylpropane. 3D formula condensed formula 2D formula (ambiguous) H H H H H H H C4H10 C C H C C C H H C H condensed line formula H (CH ) CHCHor (CH ) CH H C H C H 3 2 3 3 3 H H H H H There are a lot of ways to write this as a 2D carbon skeleton on a piece of paper. C C C C C C C C C C C C C C C C These are all representations of the same structure, but different from our first four carbon structure. These two molecules have exactly the same formula C4H10 but they are not at all the same in their physical properties. The melting points, boiling points, densities and heats of formation are given below to emphasize this. Their spectra and chemistry would not be expected to be just alike either (and it's not). This should not be surprising. Think about how you would interact with the world if one of your arms was attached where your belly button is. melting boiling heat of point point density formation butane, CH3CH2CH2CH3 -138 -1 0.579 -30.4 2-methylpropane, CH3CH(CH3)2 -159 -12 0.549 -32.4 (isobutane) We refer to these two different compounds, having identical molecular formulas, as isomers (equal units). Isomers can be different in the connectivity of the atoms; that is their skeletons are different. Or, isomers can have the same connectivity of atoms, but differ in their orientation in space (stereoisomers). To try and visualize this, think of your left hand and your right hand. Both hands have the same types of fingers, but pointing in different directions in space, with important consequences for how you interact with the world. In this example, since both four carbon alkanes have different skeletal connections, we call them structural or skeletal or constitutional isomers. We will encounter other types of isomers as we progress on our journey through organic chemistry. 4 Lecture 6 5. pentane isomers: C5H12 As before, we will begin with a five carbon straight chain isomer. There are 12 additional bonding sites, all filled with a hydrogen atom. C5H12 is saturated and it is ambiguous. condensed formula 2D formula 3D formula (ambiguous) H H H H H H H H H H H Rotation is possible C5H12 about any of the condensed line C C C carbon-carbon single formula H C C C C C H H C C H bonds, generating different conformations. CH3CH2CH2CH2CH3 H H H H H Build a model and try it. pentane H H H H Each C-C single bond can be rotated so, again, there are a variety of ways to represent these five carbons, some of which are shown. C C C C C C C C C C C C C C C C C C C C C C C C C We can shorten this chain by one carbon atom (the longest chain is now four carbon atoms) and attach the one extra carbon atom at a nonterminal position to create a second isomer. There is only one additional isomer resulting from this operation. H These are identical structures. H3C C CH2 CH3 Make models and turn one of 2 1234 a 1 3 4 them around and superimpose C C C C CH3 them on top of one another.
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