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CHEM 238 PRACTICE SOLUTION COMPLETE QANDA STUDY REVIEW PACK

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CHEM 238 PRACTICE SOLUTION COMPLETE QANDA STUDY REVIEW PACK

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CHEM 238 PRACTICE SOLUTION
COMPLETE QANDA STUDY REVIEW PACK

●● HX (HCl, HBr, HI)
Answer: Hydrohalogenation — Double bond removed, halide added to
most substituted carbon


●● HBr, radical initiator
Answer: Radical hydrohalogenation — Double bond removed, Br added
to least substituted carbon (anti-Markovnikov)


●● Br2
Answer: Halogenation — Double bond removed, two Br added anti
(vicinal dihalide)


●● Br2, H2O
Answer: Halohydrin formation — Double bond removed, Br and OH
added anti, OH on more substituted carbon


●● B2H6
Answer: Hydroboration-oxidation — Double bond removed, OH ends
up on least substituted carbon

, ●● H2O2, NaOH
Answer: Hydroboration-oxidation — Oxidizes boron to alcohol


●● Hg(OAc)2, H2O
Answer: Oxymercuration — Double bond removed, OH added
Markovnikov without rearrangements


●● NaBH4
Answer: Oxymercuration-reduction — Replaces Hg with H


●● H2, Pd/C
Answer: Alkene hydrogenation — Double bond removed, H added syn


●● Lindlar catalyst
Answer: Alkyne hydrogenation — Alkyne reduced to cis-alkene


●● Na, NH3
Answer: Alkyne reduction — Alkyne reduced to trans-alkene


●● SO2Cl + Pyridine/Et3N
Answer: Sulfonyl chloride Alcohol → chloride — O attaches to SO2 to
form good LG

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