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chem213 exam 2 rxn's

Terms in this set (12)

3° carbon with LG reacting with a weak base
SN1 rxn, Nu can bind in place of a non-hydrogen substituent AND LG (racemic if stereochemistry)
1° or 2° carbon with LG reacting with a weak base
SN2 rxn, Nu must bind on opposite side of LG.

Sub LG with Nu, change plane of Nu
1° 2° or 3° alkyl halide reacting with a strong base
E2 rxn, double bond forms b/w ALPHA carbon and BETA carbon, results in TRANS molec
3° carbon bonded to alcohol reacting to monoprotic acid
SN1 rxn, racemic mixture if stereochemistry
Alcohol with 2 OH groups, one 1° and one 3° reacting with a strong oxidizer (ex. PCC)
alcohol oxidation rxn, only 1° and 2° alcohols get oxidized, both 1° carbon and OH lose a hydrogen to form C=O
Ether reacting with a monoprotic strong acid
ether cleavage rxn, makes alcohol and R2-Nu molec
benzene bonded to a meta-director reacting with (NO2+) HNO3/H2SO4
nitration rxn, NO2+ binds meta to the director
benzene bonded to a ortho,para-director reacting with an alkyl halide in Lewis acid catalyst (usually AlCl3)
F-C alkylation rxn, bind Cl to catalyst, alkyl group binds ortho(next to) and para(opposite) to the director
synthesis for alkene > trans-glycol addition
alkene has to react with MCPBA to make an epoxide.

epoxide reacts with WATER IN ACIDIC CONDITIONS.

oxygen is protonated, most substituted C-O bond is broken,
positive charged carbon binds with water,
and another water molecule deprotonates a hydrogen.

creates TRANS-GLYCOL molec
synthesis for benzene > meta halide to the director (ex: SO3H)
sulfonation rxn,

benzene reacts with SO3 in hot acidic conditions (SO3/fuming H2SO4),
a double bond from benzene is broken to bond with S,
a S=O bond is broken to make O- (3 isomers,
double bonds within benzene move)
O- takes a hydrogen from carbon with least hydrogens, completes benzene ring again

SO3H is a meta director, molec reacts with Br2/FeBr3 and Br is added meta to the director
mechanism for alcohol reacting with a strong acid (polyprotic, H2SO4 or H3PO4)
alcohol dehydration rxn (loss of H2O)

protonate the oxygen
remove a water molecule
take a hydrogen from the carbon with least hydrogens to form double bond with the new positive carbon
mechanism for benzene reacting with acyl halide (usually RCOCl) in Lewis acid catalyst (usually AlCl3)
F-C acylation rxn

form electrophile by bonding Cl with AlCl3

a benzene double bond breaks to bond benzene to the electrophile (creates 3 isomers where the positive charge is ortho and para to electrophile)

C-H bond from the carbon that's bonded to the electrophile creates a double bond to the positive charged carbon/complete aromaticity
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