51LA Stereochem B F10 - Name: TA Name Lab Section: Day...

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1 Name: TA Name Lab Section: Day _______Time ______ OPTICAL ISOMERISM 1. Construct a model that has a central carbon atom with 4 different colored spheres attached to it, representing four different atoms or groups. Draw a solid/dashed-wedge structure of this model here and answer the following questions. C ( a blue ball ) B A D Fig. 1 a. Does the model have a plane of symmetry? Yes ______ No ______ The central carbon is said to be a stereocenter , stereogenic center, or chiral carbon. Change one of the colored spheres so that two of the four spheres are the same and examine the structure at different angles. b. Does the molecule now posses symmetry? Yes ______ No ______ What kind (plane, axis, etc.)? c. In view of your answers to a and b, what condition is necessary for a carbon to be stereogenic center? __________ d. Draw a structural formula for each of the following and indicate all chiral carbons with an asterisk: 3-chlorohexane 3-pentanol 2-amino-propanol 1,2-dibromocyclohexane 2. Reconstruct the original stereogenic carbon with the four different
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2 colored balls again. Set the model on the table so that the blue ball (C in the Fig 1) points upwards. a. Looking down on the model from above, record the colors of the balls, proceeding in a clockwise direction. Construct another model that is the mirror image of the first and place it on the table with the blue ball up. b. In what direction must you proceed to observe the same order of substituents as recorded for 2a? counter-clockwise _____ clockwise _____ c. Try to superimpose the 2 models. Are they the same? Yes _____ No _____ If not, how are they different? _____________ d. What is the stereochemical term that relates these two models? e. What two important properties must the two molecules (models) each have to be related by the term that is the answer to 2d? f. On your mirror image model, switch any two groups. Is this model still the mirror image of the original model? Yes ______ No ______ g. Try to superimpose the two models. Are they superimposable? Yes ______ No______ h. What is the stereochemical term that relates these two models? ______________________________________________________________ Reconstruct your models so that they are the same as the models in 2a-e. Change the red ball on each model to a blue one (Now models contain two blue balls) i. Are the models still mirror images? Yes ______ No ______ j. Do the models have a plane of symmetry? Yes ______ No ______ If so, describe its location. k.
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51LA Stereochem B F10 - Name: TA Name Lab Section: Day...

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