ChairStructures - Surviving Chair Structures Surviving...

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Surviving Chair Structures
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Surviving Chair Structures A “How-to” Review
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Step 1: Cyclohexane in 2-D 2 groups on the ring can be Cis (on the same side) or Trans (on opposite sides)
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Step 1: Cyclohexane in 2-D 2 groups on the ring can be Cis or Trans: Cis = Same Sides or
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Step 1: Cyclohexane in 2-D 2 groups on the ring can be Cis or Trans: Trans = Opposite Sides or
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Step 1: Cyclohexane in 2-D Which is it? Cis or Trans? Br
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Step 1: Cyclohexane in 2-D Answer: One Up… One Down… Trans… Br TRANS
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Step 1: Cyclohexane in 2-D Which are they? Cis or Trans? Br CH 2 3 HO 3 H 2 N OH
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Step 1: Cyclohexane in 2-D How did you do? Br CH 2 3 HO 3 H 2 N OH CIS TRANS
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Step 2: Draw cis-1, 3- dimethylcyclohexane
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Step 2: Draw cis-1, 3- dimethylcyclohexane Start with a hexagon…
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Step 2: Draw cis-1, 3- dimethylcyclohexane … then pick a position to be #1 (and ANY position can be #1)… 1 1 1 1 or or or etc. ..
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Step 2: Draw cis-1, 3- dimethylcyclohexane … then number around the ring (CW or CCW) to find #3(since you are drawing a 1,3-disubstituted ring) 1 or 1 1 3 3
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Step 2: Draw cis-1, 3- dimethylcyclohexane … then attach the necessary groups (two methyl groups, in this case) to the #1 and #3 positions you’ve decided to use… 1 3 CH 3 3
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Step 2: Draw cis-1, 3- dimethylcyclohexane …then add stereochemistry to show the relative positions (cis = same side, trans = opposite sides). Since the compound is cis-1,3- dimethylcyclohexane, either of the answers below will be correct answers… CH 3 3 3 3 3 3
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Step 2: Draw cis-1, 3- dimethylcyclohexane … as would these, depending on where you placed your #1 and #3 positions… CH 3 3 3 H 3 C 3 H 3 C 3 H 3 C
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Step 3: Converting to a Chair structure
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Step 3: Converting to a Chair structure Chair structures are the 3-D representation of the cyclohexane ring… Remember that this view is from the side of the ring, not from above or below… close side far side
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Step 3: Converting to a Chair structure First let’s remind ourselves about the different positions on a chair structure…
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Step 3: Converting to a Chair structure Every cyclohexane chair has six carbons, three that zig-zag up and three that zig-zag down… make sure you can identify them… "up" "down"
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Step 3: Converting to a Chair structure On the positions that zig-zag UP, you will find the vertical UP AXIAL positions… on the positions that zig-zag DOWN, you will find the vertical DOWN AXIAL positions…
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Step 3: Converting to a Chair structure On the positions that zig-zag UP, you will find the (semi-horizontal) DOWN EQUATORIAL positions… on the positions that zig-zag DOWN, you will find the (semi-horizontal) UP EQUATORIAL positions…
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Step 3: Converting to a Chair structure All of the positions are shown below in one structure:
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Step 3: Converting to a Chair structure All positions, together on the ring… make sure you can find them to draw them… Fill them in on the template shown… (answer on previous slide!)
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Step 3: Converting to a Chair structure Translation required: wedges (or bold lines) in 2-D
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This note was uploaded on 12/09/2011 for the course CHEM 331 taught by Professor Chen during the Spring '11 term at Iowa Central Community College.

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ChairStructures - Surviving Chair Structures Surviving...

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