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Chemistry – Stereoisomerism – Unit 2




               By Me.
So like stereotyping?


No, this is more to do with the placement of
certain molecules/atoms on a hydrocarbon
               (always alkenes)
Ok so we know how carbon chains are labelled
                                      And if not, this is a quick recap



              On the 2nd and 3rd Carbon On the 6th Carbon atom     There are 10
               atom, there’s a Methyl   there’s a Bromine group    Carbon atoms in
                       group                                       the chain
                                                                                         On the 4th carbon
                                                                                         atom, there is a
                    2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene                     double bond, which
                                                                                         means the
                                On the 1st Carbon                                        hydocarbon is
                                there’s a Flourine
                                                   On the 8th Carbon                     unsaturated, turnin
                                      group        atom there’s a                        g it, into an alkene.
                                                     Cholrine group


                                                 H
                                             H   C    H
                                        H    H            H   Br   H   H    H   H
                                   F C C C C C C C C C C                             H
                                        H        H    H       H    H   Cl   H   H
                                         H   C   H

                                             H

Yes I made is unnecessarily
big, but ehh… you live and
learn I guess.
For now we’re just going to look at
              geometric isomerism
So what it really is, is where Alkenes are considered to have groups on either side of their
double bond, and when this occurs. The groups can be in either E or Z (yeah german words, I
don’t get it either) isomerism, which we’ll get to.




                                                         This what we’re gonna
    So looking at our earlier examplEH                   focus on.
                                             H
                                         H   C   H
                                   H     H           H    Br   H   H    H   H
                                F C C C C C C C C C C                           H
                                   H         H   H         H   H   Cl   H   H
                                    H    C   H

                                         H
H
                                            H   C   H
                                       H    H           H   Br       H   H    H   H
                                     F C C C C C C C C C C                            H
                                       H        H   H       H        H   Cl   H   H
                                        H   C   H

                                            H




       C6H10F          H                                                      H



          H
                C C                         =                    H
                                                                     C C
                      C5H9BrCl
         Notice how the 2 carbon atoms on either side
         of the double bond, now appear to have 2
         groups of atoms on each of them. This is how
         stereoisomerism can work. However it can’t
         work if….

                C6H10F         H                It can’t happen since one of the
                         C C                    carbon atoms groups consist of the
                   H             H              same molecules within each group
So..
Here’s where E-Z Isomerism comes into play


    C6H10F            H
                                                               Would be classed as an E
                C C                                            Isomerism, as it’s heaviest
        H
                      C5H9BrCl                                 groups are across from one
                                                               another.

Name: E-2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene

                                  We measure each groups
                                  “heavyness” by calculating
                                  their Mr value.


      C6H10F           C5H9BrCl                                Would be classed as Z
                C C                                            isomerism, as the
            H             H                                    heaviest groups are next
                                                               to each other.
Name: Z-2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene

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AQA Chemistry Unit 2 AS – Stereoisomerism

  • 1. Chemistry – Stereoisomerism – Unit 2 By Me.
  • 2. So like stereotyping? No, this is more to do with the placement of certain molecules/atoms on a hydrocarbon (always alkenes)
  • 3. Ok so we know how carbon chains are labelled And if not, this is a quick recap On the 2nd and 3rd Carbon On the 6th Carbon atom There are 10 atom, there’s a Methyl there’s a Bromine group Carbon atoms in group the chain On the 4th carbon atom, there is a 2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene double bond, which means the On the 1st Carbon hydocarbon is there’s a Flourine On the 8th Carbon unsaturated, turnin group atom there’s a g it, into an alkene. Cholrine group H H C H H H H Br H H H H F C C C C C C C C C C H H H H H H Cl H H H C H H Yes I made is unnecessarily big, but ehh… you live and learn I guess.
  • 4. For now we’re just going to look at geometric isomerism So what it really is, is where Alkenes are considered to have groups on either side of their double bond, and when this occurs. The groups can be in either E or Z (yeah german words, I don’t get it either) isomerism, which we’ll get to. This what we’re gonna So looking at our earlier examplEH focus on. H H C H H H H Br H H H H F C C C C C C C C C C H H H H H H Cl H H H C H H
  • 5. H H C H H H H Br H H H H F C C C C C C C C C C H H H H H H Cl H H H C H H C6H10F H H H C C = H C C C5H9BrCl Notice how the 2 carbon atoms on either side of the double bond, now appear to have 2 groups of atoms on each of them. This is how stereoisomerism can work. However it can’t work if…. C6H10F H It can’t happen since one of the C C carbon atoms groups consist of the H H same molecules within each group So..
  • 6. Here’s where E-Z Isomerism comes into play C6H10F H Would be classed as an E C C Isomerism, as it’s heaviest H C5H9BrCl groups are across from one another. Name: E-2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene We measure each groups “heavyness” by calculating their Mr value. C6H10F C5H9BrCl Would be classed as Z C C isomerism, as the H H heaviest groups are next to each other. Name: Z-2,3-dimethyle-1-fluro-6-bromo-8-chloro-dec-4-ene