Lect27_1028 - 4 / OH / H 2 O / cold or OsO 4 , pyridine...

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Ch. 8 - 1 12. Electrophilic Addition of Bromine and Chlorine to Alkenes Addition of X–X (X = Cl, Br) across a C=C bond 2 4
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Ch. 8 - 2 4 Stereochemistry Anti addition N
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Ch. 8 - 3 13. Stereospecific Reactions A reaction is stereospecific when a particular stereoisomeric form of the starting material reacts by a mechanism that gives a specific stereoisomeric form of the product
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Ch. 8 - 4 Reaction 1 Br 2 H 3 C H H CH 3 Br C H H 3 C C CH 3 Br H CCl 4 -2-Butene H 3 C Br Br CH 3 H H -2,3-Dibromobutane (a meso compound) Reaction 2 Br 2 H 3 C H CH 3 H Br C H H 3 C C H Br CH 3 CCl 4 -2-Butene Br C H CH 3 C H Br H 3 C + (a pair of enantiomers)
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Ch. 8 - 5 14. Divalent Carbon Compounds: Carbenes Methylene Methylene 2
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Ch. 8 - 6 t 3 Usually a syn(cis) addition across a C=C bond Dihalocarbene Dihalocarbene : :
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Ch. 8 - 7 2 2 2 2 Carbenoid Carbenoid
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Ch. 8 - 8 15. Oxidation of Alkenes: Syn 1,2-Dihydroxylation Overall: addition of 2 OH groups across a C=C bond Reagents: dilute KMnO
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Unformatted text preview: 4 / OH / H 2 O / cold or OsO 4 , pyridine then NaHSO 3 , H 2 O Ch. 8 - 9 Comparison of the two reagents KMnO 4 : usually lower yield and possibly side products due to over-oxidation OsO 4 : usually much higher yield but OsO 4 is extremely toxic (oxidative cleavage of C=C) Ch. 8 - 10 16. 16. Oxidative Oxidative Cleavage with Ozone Cleavage with Ozone Ch. 8 - 11 17. Electrophilic Addition of Bromine & Chlorine to Alkynes 2 2 2 Same addition as to Alkenes Ch. 8 - 12 18. Addition of Hydrogen Halides to Alkynes 3 3 3 Ch. 8 - 13 Anti-Markovnikov addition of hydrogen bromide to alkynes occurs when peroxides are present in the reaction mixture Free Radical Mechanism Chapter 10 Ch. 8 - 14 19. Oxidative Cleavage of Alkynes 2 4 3 + 2 Example OR...
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Lect27_1028 - 4 / OH / H 2 O / cold or OsO 4 , pyridine...

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