l17c

l17c - CH 203 O R G A N I C C H E M I S T R Y I Addition to...

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Addition to carbon–carbon double bonds • Problems © Bruno I. Rubio 1 CH 203 O R G A N I C C H E M I S T R Y I Addition to carbon–carbon double bonds: Problems (1) Predict the organic product(s) of the reaction of isobutylene (at right) with each of the following reagents. Assume that no carboca- tion rearrangements occur. (a) H 2 , Pt (b) Br 2 (c) HBr (d) H 2 O, H 2 SO 4 , 100 °C (e) BH 3 then H 2 O 2 , NaOH, H 2 O (f) FCO 3 H (g) Cl 2 , H 2 O (h) OsO 4 then NaHSO 3 (i) O 3 then Zn, CH 3 CO 2 H (j) O 3 then H 2 O 2 (k) Cl 2 , CH 3 CH 2 OH (2) Predict the organic product(s) of the reaction of 2- methylpent-2-ene (at right) with each of the reagents in Prob- lem (1). Indicate which reactions afford a mixture of enanti- omers. Assume that no carbocation rearrangements occur. (3) Predict the organic product(s) of the reaction of 1- methylcyclopentene (at right) with each of the reagents in Prob- lem (1). Clearly show the stereochemistry of the product(s) where appropri- ate. Indicate which reactions afford a mixture of enantiomers. Assume that no carbocation rearrangements occur. (4) Predict the organic product of the reaction of ( S )-6- methylbicyclo[4.4.0]dec-1-ene (at right) with each of the rea- gents in Problem (1). Clearly show the stereochemistry of the product where appropriate. Assume that no carbocation rearrange- ments occur. (5) Hydrogen occurs in the three isotopic forms protium ( 1 H or simply H; this is plain ol’ hydrogen), deuterium ( 2 H or D; about 0.05% of all hydrogen atoms are D atoms) and tritium ( 3 H or T; the only radioactive isotope of hydrogen). The isotopes differ in the number of neutrons in the nucleus. Except for oc-
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l17c - CH 203 O R G A N I C C H E M I S T R Y I Addition to...

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