HANDOUT 1-Must know-Reactions

HANDOUT 1-Must know-Reactions - 1.Reactionsofalkenes H H H...

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HANDOUT-1- Reactions to know from CHM 2210-  Absolute must 1.  Reactions of alkenes: H H Br 2 H + /H 2 O H 2 /Pt BH 3 /THF H 2 O 2 /HO - Br H Br H MCPBA CH 2 Cl 2 O AntiMarkovnikov Markovnikov OH H H H Br H H H H H H H H H OH H reduction oxidation or epoxidation alcohol dihalides alkyl halide alcohol HBr ROOR H H H Br Markovnikov AntiMarkovnikov HBr 2. Preparation of alkynes: H H Br 2 R Br H Br H H 2 NaNH 2 RC CH R H
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3. Reactions of alkynes: H 2 Lindlar (siam) 2 BH/THF H 2 O 2 /HO - Hg 2+ Br Br H AntiMarkovnikov Markovnikov H H H O H H H partial reduction O H NaNH 2 C RCH 2 X primary only O R OH R R Ketone Aldehyde H + /H 2 O Br 2 H 2 /Pt H 3 C CH 3 alkane alkene 4.  Free radical reactions: bromination occurs predominantly at the most substituted carbon or otherwise  stabilized (by resonance)
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Me Me Me H Br 2 /light or NBS/light Me Me Me Br Br 2 /light or NBS/light Br not Br Br 2 /light or NBS/light Br not Br Br not Me Me H Br Br not 5. Eliminations: For eliminations (if you must) use potassium t-butoxide, to prevent substitution and get more 
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