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Iodochlorination of Styrene 1 Hexene: Characterization by NMR

Aim. Do iodochlorination reaction with styrene and 1 ? hexene.Characterize the products with NMR spectroscopy.. Introduction. Today's experiment is an example of regioselective reaction.. Regioselective Rn. Reagents and alkenes can be classified as either symmetric or unsymmetric with respect to ad

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Iodochlorination of Styrene 1 Hexene: Characterization by NMR

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    2. Aim Do iodochlorination reaction with styrene and 1 – hexene. Characterize the products with NMR spectroscopy.

    3. Introduction Today’s experiment is an example of regioselective reaction.

    4. Regioselective Rn Reagents and alkenes can be classified as either symmetric or unsymmetric with respect to addiction reaction. If a reagent or an alkene is symmetric, only one addition product is possible. If both the reagent and alkene are unsymmetric, two products are possible.

    5. Regioselective Rn Styrene and 1-Hexene are unsymmetric alkene. Potassium dichloroiodate is also unsymmetric. You may get two products and these are called regioisomer.

    6. Regioselective If a reaction of this type gives only one of the two possible regioisomer, it is said to regiospecific. If it gives mainly one product, its said to be regioselective.

    7. Regiospecific-example

    8. Regioselective-example

    9. Procedure Take 5 mL of CH2Cl2 and add 0.12 mL of styrene in a clean and dry conical flask. Add 0.33 g of potassium dichloroiodate to the mixture. Swirl it for 15 minutes. Transfer into a separatory funnel. Wash it with 3 mL of aqueous 5 % potassium sulfate solution until decolorization occur.

    10. Procedure Then wash it with 3 mL of water. Take a fresh, dry glass funnel; add 0.5 g of magnesium sulfate and filter the bottom layer through a plug of cotton. Wash the cotton wool with 3 mL more CH2Cl2. Evaporate the CH2Cl2 on a steam bath.

    11. Procedure Recrystallize residue in hexane(~ 5 mL). Calculate the % of yield. Do the same experiment with 1 – Hexene. Record the NMR spectrum. Lab manual has the chemical shift values for the possible products.

    12. Notes Do not spill the potassium dichloroiodate on benches, balances. Use non-metal spatulas to handle potassium dichloroiodate Use CH2Cl2 carefully. Do not forget to add boiling chips to the solution when you use steam bath.

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