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z-Ch. 19 Aldehydes and Ketones
CHM2211 Dr. Elsheimer Fall 09
39
Organic Chemistry
Undergraduate 2
09/30/2009

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Cards

Term
1.O3/2.Zn,H2O (terminal alkene)
Definition
C=C-C -> =O + O=C-C
Term
PCC/CH2Cl2 (primary alcohol)
Definition
C-C-OH -> C-C=O
Term
AlCl3 (bezene + aldehyde hailide)
Definition
Benzene + O=C-Cl -> Benzaldehyde
Term
BH3/OH (alkyne)
Definition
propyne -> C-C-C=O (enol totomerism)
Term
1. DIBAH -78C toluene/ 2. H3O+
Definition
ester -> aldehyde + primary alcohol
Term
1.O3/2.Zn,H2O (tertiary alkene)
Definition
two keytones
Term
KMnO4/H3O (tertiary alkene)
Definition
two keytones
Term
PCC/CH2Cl2 (secondary alcohol)
Definition
keytone
Term
KMnO4/H3O+ (secondary alcohol)
Definition
keytone
Term
CrO3/acetone H3O+ (secondary alcohol)
Definition
keytone
Term
Na2Cr2O7/CH2CO2H (secondary alcohol)
Definition
keytone
Term
HgSO4/H2SO4 (alkyne)
Definition
keytone (enol totomerism)
Term
AlCl3 (bezene + keytone hailide)
Definition
Benzene + R-O=C-Cl -> Phenyl methanal
Term
1. Li (R)2Cu/ 2. H3O+
Definition
R'-C=O-Cl -> R'-C=O-R
Term
Aldehyde + H2O
Definition
1,1 diol
Term
Aldehyde + NaOH/H2O
Definition
1,1 diol
Term
Aldehyde + H3O+
Definition
1,1 diol
Term
Aldehyde or Keytone + NaCN/HCN
Definition
Nucliophilic addition 1-ol 1-CN
Term
R-CN + 1.LiAlH4/2.H2O
Definition
R-C-NH2
Term
R-CN + H3O+/heat
Definition
R-COOH
Term
Aldehydes vs. Keytones (reactivity)
Definition
Aldehydes more reactive. (steric hinderance, R- groups electron donating)
Term
C=O + 1.CH3MgBr/2.H3O+
Definition
C-C-OH primary alcohol
Term
R-C=O + 1.CH3MgBr/2.H3O+
Definition
R-CH-OH-CH3 secondary alcohol
Term
R-C=O-R' + 1.CH3MgBr/2.H3O+
Definition
R-C-OH-C-R' tertiary alcohol
Term
R-C=O-O-C + 1.CH3MgBr/2.H3O+
Definition
Tertiary alcohol + Primary alcohol
Term
Wolff-Kishner reduction
Definition
H2NNH2/KOH R-C=O-R' -> R-CH2-R' R-C=O-H -> R-CH3
Term
Clemmensen Reduction
Definition
HCl/Zn(Hg) R-C=O-R' -> R-CH2-R' R-C=O-H -> R-CH3
Term
H2NCH3/H3O+
Definition
R-C=O-R' -> R-C=(NCH3)-R'
Term
HN(CH3)2/H3O+
Definition
R-C=O-R' -> R=C-N(CH3)2-R'
Term
Hemi-Acetal
Definition
R-C=O-R' -HCl/R"OH-> R-C-(OH)-(OR")-R'
Term
Acetal
Definition
R-C=O-R' -HCl/excess R"OH-> R-C-(OR")-(OR")-R'
Term
HOR"O'H/HCl
Definition
R-C=O-R' -> R-C-O-R"-O'-(first C) cyclic
Term
Protecting ketone from reduction
Definition
To protect: HOROH/Hl To deprotect: H3O+
Term
Wittig Reactions
Definition
(Ph)3P+-C(-)R2 + R'-C=O-R" -> R"R'-C=CR2
Term
1.AgNO3,NH3/2.H3O+
Definition
Aldehyde -> Carboxilic acid (Tollen's reagent. Only works on aldehydes)
Term
Cannizarro Rxn
Definition
Benzaldehyde -1.NaOH 2.Whatever you start with 3.H3O+-> Benzyl alcohol + Benzaldehyde
Term
-al
Definition
aldehyde
Term
-one
Definition
ketone
Term
Tollens
Definition
1.AgNO3, NH3/2.H3O+ On aldhydes only to carboxylic acid
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