有机化学英文课件chapter1
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有机化学英文原版ppt
Number of Covalent Bonds to an Atom Atoms with one, two, or three valence electrons form one, two, or three bonds Atoms with four or more valence electrons form as many bonds as they need electrons to fill the s and p levels of their valence shells to reach a stable octet
1.1 Atomic Structure
Structure of an atom
Positively charged nucleus (very dense, protons and neutrons) and smal (10-15 m) Negatively charged electrons are in a cloud (10-10 m) around nucleus Diameter is about 2 × 10-10 m (200 picometers (pm)) [the unit angstrom (Å) is 10-10 m = 100 pm]
1.5 The Nature of the Chemical Bond
Atoms form bonds because the compound that results is more stable than the separate atoms Ionic bonds in salts form as a result of electron transfers Organic compounds have covalent bonds from sharing electrons (G. N. Lewis, 1916) Lewis structures shown valence electrons of an atom as dots Hydrogen has one dot, representing its 1s electron Carbon has four dots (2s2 2p2) Stable molecule results at completed shell, octet (eight dots) for main-group atoms (two for hydrogen)
有机化学英文课件
+ C H 3 C H 2 -O -H + C H 3 C H 2 -O -H
SN 2
+ C H 3 C H 2 -O -C H 2 C H 3 + O -H
H
H
H
A new oxonium ion
11-11
Preparation of Ethers
Step 3: proton transfer to solvent completes the reaction
+
CH 3 CH 2 -O -CH 2 C H 3 + O -H
H
H
proton tran sf er
+ CH 3 CH 2 -O -CH 2 C H 3 + H O -H
H
11-12ቤተ መጻሕፍቲ ባይዱ
Preparation of Ethers
Acid-catalyzed addition of alcohols to alkenes
Acid-catalyzed dehydration of alcohols
• diethyl ether and several other ethers are made on an industrial scale this way
• a specific example of an SN2 reaction in which a poor leaving group (OH-) is converted to a better one (H2O)
CH 3 CH3C=CH2 + H
+ O CH3
H
CH3 C H 3 C+C H 3 +
有机化学英文课件chapter6-78页PPT精选文档
Energy Diagrams
u Energy diagram: a graph showing the changes in energy that occur during a chemical reaction
u Reaction coordinate: a measure in the change in positions of atoms during a reaction
• Markovnikov’s rule: in the addition of HX, H2O, or ROH to an alkene, H adds to the carbon of the double bond having the greater number of hydrogens
6-16
is n o t s u p p o r te d
• exergonic reaction: a reaction in which the Gibbs free energy of the products is lower than that of the reactants; the position of equilibrium for an exergonic reaction favors products
M a c in to s h P IC T im ag e fo rm at
is n o t su p p o rted
6-4
Reaction Mechanisms
u A reaction mechanism describes how a reaction occurs
• which bonds are broken and which new ones are formed
有机化学 英文课件 chapter(2)
is n o t s u p p o rte d
7-20
Hydroboration
7-2
Nomenclature
IUPAC: use the infix -yn- to show the presence of a carbon-carbon triple bond
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
7-8
Alkylation of Alkyne Anions
• alkylation of alkyne anions is the most convenient method for the synthesis of terminal alkynes
Organic Chemistry
William H. Brown Christopher S. Foote Brent L. Iverson
7-1
Alkynes
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
Chapter 7
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
• reaction of the vinylic cation (an electrophile) with halide ion (a nucleophile) gives the product
7-20
Hydroboration
7-2
Nomenclature
IUPAC: use the infix -yn- to show the presence of a carbon-carbon triple bond
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
7-8
Alkylation of Alkyne Anions
• alkylation of alkyne anions is the most convenient method for the synthesis of terminal alkynes
Organic Chemistry
William H. Brown Christopher S. Foote Brent L. Iverson
7-1
Alkynes
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
Chapter 7
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
• reaction of the vinylic cation (an electrophile) with halide ion (a nucleophile) gives the product
有机化学课件1, INTRODUCTION
B ulletproof!
7
1.1 Concept Development of Organic Chemistry
1770, Organic and Inorganic, T. Bergman (Sweden) 1806, Organic Chemistry, J. Berzelius (柏则里)(Germany) 1828, Preparation of urea from ammonium cyanate (F. Wohler, Germany)
Conjugate base Conjugate acid
Ka=[HB][A:]/[HA][B]
2. The Lewis Definition
A Lewis acid is a substance that accepts an electron pair and a Lewis
base is a substance that donates an electron pair.
C l C l A l
C H 3 +O
C l C H 3 C l A l O
C l
C H 3
C l C H 3
Lewis Acid
Lewis base
24
Equilibrium favors reaction of the stronger acid and stronger base to give the weaker acid and weaker base
2
CHAPTER 1, INTRODUCTION
Organic Chemistry: Natural science, Life science, Medicine Materials science, Polymeric materials Fine chemicals, Chemical industry
7
1.1 Concept Development of Organic Chemistry
1770, Organic and Inorganic, T. Bergman (Sweden) 1806, Organic Chemistry, J. Berzelius (柏则里)(Germany) 1828, Preparation of urea from ammonium cyanate (F. Wohler, Germany)
Conjugate base Conjugate acid
Ka=[HB][A:]/[HA][B]
2. The Lewis Definition
A Lewis acid is a substance that accepts an electron pair and a Lewis
base is a substance that donates an electron pair.
C l C l A l
C H 3 +O
C l C H 3 C l A l O
C l
C H 3
C l C H 3
Lewis Acid
Lewis base
24
Equilibrium favors reaction of the stronger acid and stronger base to give the weaker acid and weaker base
2
CHAPTER 1, INTRODUCTION
Organic Chemistry: Natural science, Life science, Medicine Materials science, Polymeric materials Fine chemicals, Chemical industry
有机化学结构与功能第一章
Functional groups determine the reactivity of organic molecules
The structure of the molecule is related to the reactions that it can undergo
What is organic synthesis? Organic synthesis is the making of new organic molecules
有 机化
H
C Br
Cl F
1
学
Chapter 1 Structure and Bonding In Organic Molecules
1-1 1-2 1-3 1-4 1-5 1-6 1-7 1-8 1-9 The Scope of Organic Chemistry: An Overview Coulomb Forces: A Simplified View of Bonding Ionic and Covalent Bonds: The Octet Rule Electron-Dot Model of Bonding: Lewis Structures Resonance Forms Atomic Orbitals: A Quantum Mechanical Description Molecular Orbitals and Covalent Bonding Hybrid Orbitals: Bonding in Complex Molecules Structures and Formulas of Organic Molecules
14
Elements tend to form molecules in such a way
The structure of the molecule is related to the reactions that it can undergo
What is organic synthesis? Organic synthesis is the making of new organic molecules
有 机化
H
C Br
Cl F
1
学
Chapter 1 Structure and Bonding In Organic Molecules
1-1 1-2 1-3 1-4 1-5 1-6 1-7 1-8 1-9 The Scope of Organic Chemistry: An Overview Coulomb Forces: A Simplified View of Bonding Ionic and Covalent Bonds: The Octet Rule Electron-Dot Model of Bonding: Lewis Structures Resonance Forms Atomic Orbitals: A Quantum Mechanical Description Molecular Orbitals and Covalent Bonding Hybrid Orbitals: Bonding in Complex Molecules Structures and Formulas of Organic Molecules
14
Elements tend to form molecules in such a way
有机化学01-Lecture
A polar covalent bond has a slight positive charge on one end and a slight negative charge on the other
A Polar Bond Has a Dipole Moment
A polar bond has a negative end and a positive end
The synthesis of the simple organic compound urea in 1828 showed that organic compounds can be prepared in the laboratory from non-living material.
Today, organic natural products are routinely synthesized in the laboratory.
Molecular weight: the sum of the atomic weights of all the atoms in the molecule
The Distribution of Electrons in an Atom
Quantum mechanics uses the mathematical equation of wave motions to characterize the motion of an electron around a nucleus.
Nitric Oxide Radical, Mammalian Signaling Agent
Radical
Carbocation
Carbene
Borane
有机化学英文chapter(2)幻灯片
Macintosh PICT image format
is not supported
• because water is a stronger acid than terminal alkynes, hydroxide ion is not a strong enough base to convert a terminal alkyne to an alkyne anion
image format is not supported
7-8
Alkylation of Alkyne Anions
• alkylation of alkyne anions is the most convenient method for the synthesis of terminal alkynes
is not supported
7-16
Addition of HX
Alkynes undergo regioselective addition of
either 1 or 2 moles of HX, depending on the
ratios in which the alkyne and halogen acid
Addition of borane to an internal alkyne gives a trialkenylborane
• addition is syn stereoselective
Macintosh PICT image format
is not supported
7-20
Hydroboration
- HBr R A haloalkene (a vinylic halide)
is not supported
• because water is a stronger acid than terminal alkynes, hydroxide ion is not a strong enough base to convert a terminal alkyne to an alkyne anion
image format is not supported
7-8
Alkylation of Alkyne Anions
• alkylation of alkyne anions is the most convenient method for the synthesis of terminal alkynes
is not supported
7-16
Addition of HX
Alkynes undergo regioselective addition of
either 1 or 2 moles of HX, depending on the
ratios in which the alkyne and halogen acid
Addition of borane to an internal alkyne gives a trialkenylborane
• addition is syn stereoselective
Macintosh PICT image format
is not supported
7-20
Hydroboration
- HBr R A haloalkene (a vinylic halide)
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• s (one per shell) • p (set of three per shell 2 and higher) • d (set of five per shell 3 and higher) .....
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-3
Schematic View of an Atom
• a small dense nucleus, diameter 10-14 - 10-15 m, which contains positively charged protons and most of the mass of the atom
• only two electrons can occupy an orbital and their spins must be paired
Hund’s Rule:
• when orbitals of equal energy are available but there are not enough electrons to fill all of them, one electron is added to each orbital before a second electron is added to any one of them
1-12
Electronegativity
Electronegativity:
• a measure of an atom’s attraction for the electrons it shares with another atom in a chemical bond
Pauling scale
• each shell can hold 2n2 electrons (n = 1,2,3,4......)
M acin to sh P IC T im ag e fo rm at
is n o t su p p o rted
1-5
Electron Configuration of Atoms
Shells are divided into subshells called orbitals, which are designated by the letters s, p, d, f,........
M acintosh PIC T im age form at
is not supported
1-2
Organic Chemistry
The study of the compounds of carbon Over 10 million compounds have been identified
• in forming Na+F-, the single 3s electron from Na is transferred to the partially filled valence shell of F
M
a c in t o s h
im
ag e
fo r
is
not
su p p
P
IC
T
m
at
1-7
Electron Configuration of Atoms
The pairing of electron spins
1-8
Electron Configuration of Atoms
Table 1.3 The Ground-State Electron Configuration of Elements 1-18
• we use a single-headed (barbed) curved arrow to show the transfer of one electron from Na to F
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
Table 1.4 Lewis Dot Structures for Elements 1-18
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-11
Lewis Model of Bonding
Atoms bond together so that each atom acquires an electron configuration the same as that of the noble gas nearest it in atomic number
1-13
Formation of Ions
A rough guideline:
• ions will form if the difference in electronegativity between interacting atoms is 1.9 or greater
• example: sodium (EN 0.9) and fluorine (EN 4.0)
M acintosh PIC T im age form at
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Chapter 1
M acintosh P IC T im age form at
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M acintosh P IC T im age form at
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o r te d
1-14
Covalent Bonds
The simplest covalent bond is that in H2
• the single electrons from each atom combine to form
an electron pair
M a c in t o s h
1-9
Lewis Dot Structures
Gilbert N. Lewis Valence shell:
• the outermost occupied electron shell of an atom
Valence electrons:
• electrons in the valence shell of an atom; these electrons are used to form chemical bonds and in chemical reactions
3.0 - 2.1 = 0.9 • we show polarity by using the symbols d+ and d-, or by
using an arrow with the arrowhead pointing toward the negative end and a plus sign on the tail of the arrow at the positive end
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-16
Polar and Nonpolar Covalent Bonds
• an example of a polar covalent bond is that of H-Cl • the difference in electronegativity between Cl and H is
to complete its valence shell; a chemical bond formed by sharing electrons is called a covalent bond • bonds may be partially ionic or partially covalent; these bonds are called polar covalent bonds
Although all covalent bonds involve sharing of electrons, they differ widely in the degree of sharing We divide covalent bonds into
• nonpolar covalent bonds • polar covalent bonds
1-6
Electron Configuration of Atoms
Aufbau Principle:
• orbitals fill in order of increasing energy from lowest energy to highest energy
Pauli Exclusion Principle:
• generally increases left to right in a row • generally increases bottom to top in a column
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
P IC T
im a g e
fo r m a t
is
not
s u p p o r te d
• the shared pair functions in two ways simultaneously; it is shared by the two atoms and fills the valence shell of each atom
Organic Chemistry
William H. Brown Christopher S. Foote Brentng & Shapes of Molecules
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-3
Schematic View of an Atom
• a small dense nucleus, diameter 10-14 - 10-15 m, which contains positively charged protons and most of the mass of the atom
• only two electrons can occupy an orbital and their spins must be paired
Hund’s Rule:
• when orbitals of equal energy are available but there are not enough electrons to fill all of them, one electron is added to each orbital before a second electron is added to any one of them
1-12
Electronegativity
Electronegativity:
• a measure of an atom’s attraction for the electrons it shares with another atom in a chemical bond
Pauling scale
• each shell can hold 2n2 electrons (n = 1,2,3,4......)
M acin to sh P IC T im ag e fo rm at
is n o t su p p o rted
1-5
Electron Configuration of Atoms
Shells are divided into subshells called orbitals, which are designated by the letters s, p, d, f,........
M acintosh PIC T im age form at
is not supported
1-2
Organic Chemistry
The study of the compounds of carbon Over 10 million compounds have been identified
• in forming Na+F-, the single 3s electron from Na is transferred to the partially filled valence shell of F
M
a c in t o s h
im
ag e
fo r
is
not
su p p
P
IC
T
m
at
1-7
Electron Configuration of Atoms
The pairing of electron spins
1-8
Electron Configuration of Atoms
Table 1.3 The Ground-State Electron Configuration of Elements 1-18
• we use a single-headed (barbed) curved arrow to show the transfer of one electron from Na to F
M a c in to s h P IC T im a g e fo r m a t
is n o t s u p p o r te d
Table 1.4 Lewis Dot Structures for Elements 1-18
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-11
Lewis Model of Bonding
Atoms bond together so that each atom acquires an electron configuration the same as that of the noble gas nearest it in atomic number
1-13
Formation of Ions
A rough guideline:
• ions will form if the difference in electronegativity between interacting atoms is 1.9 or greater
• example: sodium (EN 0.9) and fluorine (EN 4.0)
M acintosh PIC T im age form at
is not supported
Chapter 1
M acintosh P IC T im age form at
is not supported
M acintosh P IC T im age form at
is not supported
o r te d
1-14
Covalent Bonds
The simplest covalent bond is that in H2
• the single electrons from each atom combine to form
an electron pair
M a c in t o s h
1-9
Lewis Dot Structures
Gilbert N. Lewis Valence shell:
• the outermost occupied electron shell of an atom
Valence electrons:
• electrons in the valence shell of an atom; these electrons are used to form chemical bonds and in chemical reactions
3.0 - 2.1 = 0.9 • we show polarity by using the symbols d+ and d-, or by
using an arrow with the arrowhead pointing toward the negative end and a plus sign on the tail of the arrow at the positive end
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
1-16
Polar and Nonpolar Covalent Bonds
• an example of a polar covalent bond is that of H-Cl • the difference in electronegativity between Cl and H is
to complete its valence shell; a chemical bond formed by sharing electrons is called a covalent bond • bonds may be partially ionic or partially covalent; these bonds are called polar covalent bonds
Although all covalent bonds involve sharing of electrons, they differ widely in the degree of sharing We divide covalent bonds into
• nonpolar covalent bonds • polar covalent bonds
1-6
Electron Configuration of Atoms
Aufbau Principle:
• orbitals fill in order of increasing energy from lowest energy to highest energy
Pauli Exclusion Principle:
• generally increases left to right in a row • generally increases bottom to top in a column
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
P IC T
im a g e
fo r m a t
is
not
s u p p o r te d
• the shared pair functions in two ways simultaneously; it is shared by the two atoms and fills the valence shell of each atom
Organic Chemistry
William H. Brown Christopher S. Foote Brentng & Shapes of Molecules