AP Chemistry . A. Allan . Chapter 4 Notes - Types of Chemical Reactions and Solution Chemistry . 4.1 Water, the Common Solvent . A. Structure of water
B.Sc. - FIRST YEAR CHEMISTRY SESSION - 2011-12 There shall be three written papers and a practical examination as follows: Max. Marks Paper – I Inorganic Chemistry 50
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Volatile compounds of silicon and aluminium, such as hydrides, alkyls, halides, and alkoxides, serve as pre-cursors to oxides in chemical vapor deposition (CVD)
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Download like anti-mutagenic, anti-tumor and anti-helminthic. The main objectives of this research were to determine bioactive compounds in agarwood leaves; leaves extract and oil yield obtained from maceration and soxhlet extraction methods re
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Download like anti-mutagenic, anti-tumor and anti-helminthic. The main objectives of this research were to determine bioactive compounds in agarwood leaves; leaves extract and oil yield obtained from maceration and soxhlet extraction methods re
Download like anti-mutagenic, anti-tumor and anti-helminthic. The main objectives of this research were to determine bioactive compounds in agarwood leaves; leaves extract and oil yield obtained from maceration and soxhlet extraction methods re
transition metals will form cations with more than one possible charge. The following Periodic Table shows the charges for metal cations commonly found in ionic compounds: 1A. 2A. Transition Elements (B). 3A. 4A. 5A. H+1. Li+1. Be+2. Na+1. Mg+2. Al+3
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TYPES OF CARBONYL COMPOUNDS� General formula
Name
Name suffix -al
O
Aldehyde
C
R
Name
General formula O
Ester
H
R
C
O�
Ketone
C�
R
Acid anhydride
R'
O
Carboxylic acid� Acid halide
-one
R
C
O
O
-oyl halide
X=halogen
C
R
X
O R
C
O� O
C
Lactone (cyclic ester)
-oic acid
H
-oic anhydride R
Name suffix -oate
O O C
R'
O
O
Amide
R
Lactam� (cyclic amide)
C
N
-amide
R' R"
O C
N
R'
Detergents and "fatty acids" - amphiphilic molecules CO2
hydrophobic
hydrophilic
CO2H
omega-3-fatty acid
H2O H2O
H2O
Phospholipids - Fatty acid esters of glycerol
grease OH
H2O H2O
OH
glycerol a triol
OH H2O
MICELLE O O
O
O
LIPID BILAYER
O O P O O
NH3
Phosphatidylcholine
O
Amides in Peptides and Proteins
OH
O
NH2
a OH
H2N
OH
H2N
O
O
glycine
alanine
OH
H2N
OH
H2N
O
O
O
phenylalanine
OH
H2N
glutamic acid
asparagine
Five of the 20 amino acid building blocks that go into all proteins All a-amino acids
Proteins are polyamides H N
N H
O
Each protein is defined by a specific primary sequence of amino acids
O
O
H N
N H
O
CO2H
b -Lactam Antibiotics H2N
H
H
Other Penicillins varied at this position
S
H H N
N
O
HO2C
H
O
g-lactam
NH
Penicillin G
H
d-lactam� NH
NH
O
O
b
N
HO2C
b-lactam
H2N
S
O
6-Aminopenicillamic acid
a
H
O
OH O
b-amino acid
a
H2N
H2N
g
g
O
b a
OH
g-amino acid
d
b
OH O
d-amino acid
SUMMARY - SYNTHESIS OF ALDEHYDES AND KETONES� 1. Oxidation of alcohols � ClN H CrO3 R1�
O
R2 R1
H
R1
OH�
Na2Cr2O7 will over-oxidize to carboxylic acid
O
O
Na2Cr2O 7� H 2SO4�
OH
R1
R1
R2
R2
1. R2MgBr 2. pH7
H
R1
OH
2. From alkynes O�
O
2+
R1
H
Hg , H2 O H2 SO 4
R1
Me�
R1
H
1. RBH2 2. H2 O2, NaOH
R1
H
SUMMARY - SYNTHESIS OF ALDEHYDES AND KETONES� 3. Friedel-Crafts Acylation O Cl
O R
R
AlCl3
4. Ozonolysis 1. O3 2. Zn/H3O+
H
O
O
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 1. Nucleophilic Addition: Reactions with Aldehydes and Ketones (Chapter 19) O
A.� R
-O
Nu
H3O+
HO
R'� Nu
Example: Grignard Reaction�
O
Section 19.8
HO
CH3MgBr +
Example: Cyanohydrin Formation O
Section 19.7
HO
CN
HCN H
H
Nu�
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 1. Nucleophilic Addition A. Hydration and Acetal Formation O
H2O
HO
OH
OH
O
O
HO
H3O+ Section 19.11
Section 19.6
O R
H
O
O
R�
H
+
OH OH
Electrophilic at C
H
No longer electrophilic at C�
OH R
HO
OH OH
H
HO
OH OH
R
H
HO
R
O
O
O
H
R
H
H2O
O
R
H
Protected (masked) aldehyde
O
Acetals as Protecting Groups for Aldehydes�
X
H Br O
OH OH
H
H
BrMg O
+
H Br
M go
O
Mgo
O
H BrMg
electrophile
O
O O
1.
H
2. pH7 H OH
O
H
H2O/H+
OH
O
O
Overview of Reactions 4/27-5/9 - Reactions with carbonyls 1. Nucleophilic Addition A.
CH3-Br
BuLi P
P
CH3
P
CH2
O
triphenyl phosphine
Ph3P Wittig Reaction
Section 19.12
Ph3PO
CH2
O
Ph = Phenyl
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 1. Nucleophilic Addition O
B. R
-O
Nu
H3O+
H2O
Nu
Nu R
R' Nu
R'
Overview of Reactions 4/27-5/9 - Reactions with carbonyls 1. Nucleophilic Addition B. continued Example: Imine Formation H
O
O NH2
H2O
H3O+
H
NH
H H2N
H
H N
H2O NH
Sometimes called a Schiff base in biochemistry
H
NH
Section 19.9
SUMMARY - Synthesis of Carboxylic Acids� 1.
Oxidative cleavage of alkene R'
HO
KMnO4
HO O
R
2.
R
O R'
Oxidation of 1 alcohols and aldehydes O� R
H OH
R
H R
3.
O�
Jones Oxidation�
OH�
H
Carboxylation of Grignard Reagents O� RMgBr�
CO2� R
OH�
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 2. Nucleophilic Acyl Substitution: Reactions with Carboxylic Acid derivatives (Chapter 21) O R
-O
O
Nu Y
Y
-
R
Nu
Y Nu Y = Leaving Group
O
LiAlH4 OR
O
RO-Li+
LiAlH4 H
O OR
Ester hydride reduction Chapter 17.5
H
nucleophilic substitution
MeMgBr
OH
nucleophilic addition
O
RO-Li+�
nucleophilic substitution
MeMgBr Me
OH Me Me
nucleophilic addition�
Ester grignard reaction Section 21.6
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 2. Nucleophilic Acyl Substitution Carboxylic Acid Derivatives
Example:Acyl Halide Section 21.4 O
OH
O
Example:Ester Section 21.6 O
Cl
OH
SOCl2
O
OEt
CH3CH2OH HCl
O
Cl
O
NHR2
NR2
Example:Amide Section 21.7
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 3. Alpha Substitution: Enolate/Enol Chemistry O
O
O
H must have "a " H (pKa 10-20)
E+ = electrophile
enolate
O E
OH
OH
enol
OH
Br2
O Br
O
H
LDA (base)
Alpha Halogenation Section 22.3
OLi
Alpha Alkylation Section 22.8
O CH3I LDA =
Li N
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 4. Condensation Reactions: Enolate/Enol Chemistry O
O
O
base�
R'�
R
R
OH
R' R''
O
R''
R
H
Aldol Reaction O
Section 23.2-23.7
OH
O
base
O H�
CH3
H
H3C Claisen Condensation
O EtO
H
C H2
H�
Section 23.8-23.9
O
O
base CH3
H3C
CH2
O
EtO
+
O
CH2
H3C
O
H3C OEt
C H2
OEt -
OEt
Key in fatty acid biosynthesis
Overview of Reactions 4/27-5/9 - Reactions with carbonyls� 4. Condensation Reactions: Enolate/Enol Chemistry continued� Section 23.11�