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HBr
O Br HO
CH3 CH3
alkene
*SN2 like
Intramolecular OH NaOH O
Williamson Br *forms O- that attacks
halogenated C
OH
NaOH H3C O
H3C
Cl
NBS
60oC
transition state
CH3 CH3
. CH3
CH3
. CH3 CH3
Br
Conjugated *in this example we will examine the *Low T: more stable TS
Systems case of HBr
*High T: more stable
compound
H2C CH2
*NOTE: If more than one
H3O+
HBr conjugated system
Br2
possibly exists, examine
H2C
Br Br
transition state
+ +
D D
W
heat
+
W
Facilitator: Chris Lovero Organic Chemistry II Reactions 3
NOTE: FROM HERE, YOU HAVE TO KNOW YOUR META, ORTHO, AND PARA DIRECTORS
Task Reaction Notes
*X = Cl or Br
Halogenation of X
Benzene X2, FeX3 or
(I2 / CuCl2)
H2SO4 heat
*REVERSIBLE DUE TO
Sulfonation SO 3H
(fuming sulfuric) SO3 / H2SO4 ENTROPY
heat
SO 3H
+ H2SO 4
+ H2O
*watch rearrangement!
Friedel-Crafts
Alkylation *no strong deactivators
R
RCl (no strong W grps)
AlCl3
Halides: 2) H3O+
*formation of benzyne
in mechanism
Elimination /
Addition X NH2 * Nu can be OH-, RO-,
-
NH2 NH2.
NaNH2 /
+ *will get a mixture (like
NH3 (l) second example)
*8 different stereochems
Chlorination of Cl
Benzene actually occur
3 Cl2 / heat Cl Cl *this particular molecule
Cl Cl compound Rid
Cl (lice killer)
Catalytic
Hydrogenation
3 H2 / 1000 psi / 100oC
Ru or Rh (Pt,Pd,Ni also)
KMnO4/H2O groups.
O
OH-/100oC
HO2 C CO2 H
CO2 H
Na2Cr2O7 / H2SO4
stable
I
NaI
Br *SN2
acetone
CH3CH2O-
*E2
Na+
-
Rxns of phenols NaOH O *2nd rxn is Fischer
similar to alochols Estherification
PBr3 OH
(no rxn)
Facilitator: Chris Lovero Organic Chemistry II Reactions 6
Task Reaction Notes
Oxidation of *This reaction forms a
Na2Cr2O7
Phenols to HO OH D-A dienophile!
O O
Quinones
H2SO4
O harsh.
OH CrO3 / H2SO4 / H2O
acetone / 0oC
(Jones reagent)
PCC
CH2Cl2
REVIEW:
Cleavage of H3C CH3 H3C CH3
Alkenes by 1) O3
Ozonolysis O + O
H CH3 2) (CH3)2S H CH3
1) Sia2BH R H H
RCH2
2) H2O2 / OH- O
H OH
either
1 mixture of ketones
R R
reagent
Facilitator: Chris Lovero Organic Chemistry II Reactions 7
Task Reaction Notes
Dithiane Synthesis *Dithiane will be given
of Aldehydes and O *BuLi =
Ketones 1) BuLi H3O+
S S S S CH3(CH2)2CH2-Li
2) R - X
HgCl2
R H
H H R H *Halide must be methyl
or 1o
1) BuLi
2) R1 - X
O
H3O+
S S 1
1 HgCl2 R R
R R
Ketones from O
Nitriles 1) R1-MgX
R C N 1
2) H3O+ R R
sheet)
H + bulky groups to be
each other.
H maj
H
Facilitator: Chris Lovero Organic Chemistry II Reactions 8
Task Reaction Notes
Aldehydes and *Aldehydes or
Ketones: O OH
- unhindered ketones
CN
Formation of R C CN
Cyanohydrins *will use this as a
R H HCN
H reagent in the future.
O OH
NaCN
H3CH2C C CN
H3CH2C H H+
H
*non AQ favors reactant
Aldehydes and
Ketones: Addition O RNH2 *AQ favors product
of 1o Amines C N R
C
H+
Wolf-Kishner O
*avoid halogens and
Reaction NH2NH2 other good LGs.
instead)
Acetal Formations
"protected
carbonyls" OEt
CH3 2(CH3CH2OH)
CH3
H+
O EtO
*aldehyde protected
*easier to just use
OH OH
before ketone because
O HO CH 3
+
1) OH OH /H it is more reactive
H 2) CH3MgBr H
O 3) H3O+ O
O -
O CH 3
H
H
O O
O O