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Chapter 20
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Carboxylic Acids
Chapter 20
*
Introduction
The functional group of carboxylic acids consists of a C?O with ?OH bonded to the same carbon.
Carboxyl group is usually written ?COOH.
Aliphatic acids have an alkyl group bonded to ?COOH.
Aromatic acids have an aryl group.
Fatty acids are long-chain aliphatic acids.
Chapter 20
Chapter 8
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Reactions of Alkenes
Chapter 8
*
Bonding in Alkenes
Electrons in pi bond are loosely held.
The double bond acts as a nucleophile attacking electrophilic species.
Carbocations are intermediates in the reactions.
These reactions are called electrophilic additions.
Chapter 8
Chapter 8
*
Electrophilic Addition
Step 1: Pi electrons attack the electrophile.
Step 2: Nucleophile attacks the carbocation.
Chapter 19
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Amines
Chapter 19
*
Biologically Active Amines
The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals.
Many drugs of addiction are classified as alkaloids.
Chapter 15
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Chaper 15
*
Conjugated Systems
Conjugated double bonds are separated by one single bond.
Isolated double bonds are separated by two or more single bonds.
Conjugated double bonds are more stable than isolated ones.
Chaper 15
Chapter 19
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Amines
Chapter 19
*
Biologically Active Amines
The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals.
Many drugs of addiction are classified as alkaloids.
Chapter 19
Chapter 18
?2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Ketones and Aldehydes
Chapter 18
*
Carbonyl Compounds
Chapter 18
Chapter 18
*
Carbonyl Structure
Carbon is sp2 hybridized.
C?O bond is shorter, stronger, and more polar than C?C bond in alkenes.
Chapter 18
Chapter 8
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Reactions of Alkenes
Chapter 8
*
Bonding in Alkenes
Electrons in pi bond are loosely held.
The double bond acts as a nucleophile attacking electrophilic species.
Carbocations are intermediates in the reactions.
These reactions are called electrophilic additions.
Chapter 8
Chapter 8
*
Electrophilic Addition
Step 1: Pi electrons attack the electrophile.
Step 2: Nucleophile attacks the carbocation.
Chapter 15
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Chaper 15
*
Conjugated Systems
Conjugated double bonds are separated by one single bond.
Isolated double bonds are separated by two or more single bonds.
Conjugated double bonds are more stable than isolated ones.
Chaper 15
Chapter 14
? 2010, Prentice Hall
Organic Chemistry, 7th Edition L. G. Wade, Jr.
Ethers, Epoxides, and Sulfides
Chapter 14
*
Ethers
Formula is R?O?R???where R and R? are alkyl or aryl.
Symmetrical or unsymmetrical
O
C
H
3
C
H
3
O
C
H
3
Chapter 14
Chapter 14
*
Structure and Polarity
Oxygen is sp3 hybridized.
Bent molecular geometry.
C?O?C angles is 110?.
Polar C?O bonds.
Dipole moment of 1.3 D.
Chapter 14
Chapter 11
*
Reaction with HBr
?OH of alcohol is protonated.
?OH2+ is good leaving group.
3? and 2? alcohols react with Br- via SN1.
1? alcohols react via SN2.
H
3
O
+
B
r
-
R
O
H
R
O
H
H
R
B
r
Chapter 11
Chapter 13
*
The N + 1 Rule
If a signal is split by N equivalent protons,
it is split into N + 1 peaks.
Chapter 13
Chapter 13
*
Equivalent protons do not split each other.
Protons bonded to the same carbon will split each other if they are nonequivalent.
Protons on adjacent carbons normally will split each other.
Protons separated by four or more bonds will not split each other.
Spin-spin Splitting Distance
Chapter 13
Chapter 12
*
IR Spectrum of Amides
Amides will show a strong absorption for the C?O at 1630?1660 cm-1.
If there are hydrogens attached to the nitrogen of the amide, there will N?H absorptions at around 3300 cm-1.
Chapter 12
*
Carbon?Nitrogen Stretching
C?N 1200 cm-1
C?N 1660 cm-1 usually strong
C?N > 2200 cm-1
For comparison, C?C < 2200 cm-1
Chapter 12
Pages
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