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Organic Chemistry. William H. Brown Christopher S. Foote Brent L. Iverson. Alkenes: Structure and Nomenclature. Chapter 5. Unsaturated Hydrocarbons. Unsaturated hydrocarbon: contains one or more carbon-carbon double or triple bonds

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organic chemistry

Organic Chemistry

William H. Brown

Christopher S. Foote

Brent L. Iverson

unsaturated hydrocarbons
Unsaturated Hydrocarbons
  • Unsaturated hydrocarbon:contains one or more carbon-carbon double or triple bonds
  • Alkene:contains a carbon-carbon double bond and has the general formula CnH2n
  • Alkyne:contains a carbon-carbon triple bond and has the general formula CnH2n-2
unsaturated hydrocarbons4
Unsaturated Hydrocarbons
  • Arenes:benzene and its derivatives (Ch 21-22)
    • we do not study arenes until Chapters 21 & 22
    • however, we show structural formulas of compounds containing the phenyl group before that time
    • the phenyl group is not reactive under any of the conditions we describe in Ch 6-20
structure of alkenes
Structure of Alkenes
  • A double bond consists of
    • one sigma bond formed by the overlap of sp2 hybrid orbitals and one pi bond formed by the overlap of parallel 2p orbitals
    • the two carbon atoms of a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 120°
structure of alkenes6
Structure of Alkenes
  • it takes approximately 264 kJ (63 kcal)/mol to break the pi bond in ethylene; that is, to rotate one carbon by 90° with respect to the other so that there is no overlap between 2p orbitals on adjacent carbons
cis trans isomerism in alkenes
Cis,Trans Isomerism in Alkenes
  • Cis,trans isomers: isomers that have the same connectivity but a different arrangement of their atoms in space due to the presence of either a ring or a carbon-carbon double bond
index of hydrogen deficiency
Index of Hydrogen Deficiency
  • Index of hydrogen deficiency (IHD): the sum of the number of rings and pi bonds in a molecule
  • To determine IHD, compare the number of hydrogens in an unknown compound with the number in a reference hydrocarbon of the same number of carbons and with no rings or pi bonds
    • the molecular formula of the reference hydrocarbon is CnH2n+2
index of hydrogen deficiency9

)

(H

- H

reference

molecule

Index of Hydrogen Deficiency
  • for each atom of a Group 7 element (F, Cl, Br, I), add one H
  • no correction is necessary for the addition of atoms of Group 6 elements (O,S) to the reference hydrocarbon
  • for each atom of a Group 5 element (N, P), subtract one hydrogen

IDH =

2

index of hydrogen deficiency10
Index of Hydrogen Deficiency

Problem: isopentyl acetate has a molecular formula of C7H14O2. Calculate its IHD

  • reference hydrocarbon C7H16
  • IHD = (16-14)/2 = 1

Problem: calculate the IHD for niacin, molecular formula C6H6N2O

  • reference hydrocarbon C6H16
  • IHD = (16 - 6)/2 = 5

O

O

Isopentyl acetate

iupac nomenclature
IUPAC Nomenclature

1. Number the longest chain of carbon atoms that contains the double bond in the direction that gives the carbons of the double bond the lowest numbers

2. Locate the double bond by the number of its first carbon

3. Name substituents

4. Number the carbon, locate and name substituents, locate the double bond, and name the main chain

common names
Common Names
  • Despite the precision and universal acceptance of IUPAC nomenclature, some alkenes, particularly low-molecular-weight ones, are known almost exclusively by their common names
common names13
Common Names
  • the common names methylene, vinyl, and allyl are often used to show the presence of the following alkenyl groups
the cis trans system
The Cis,Trans System
  • Configuration is determined by the orientation of atoms of the main chain
the e z system
The E,Z System
  • uses priority rules (Chapter 3)
  • if groups of higher priority are on the same side, the configuration is Z (German, zusammen)
  • if groups of higher priority are on opposite sides, the configuration is E (German, entgegen)
the e z system16
The E,Z System
  • Example:name each alkene and specify its configuration by the E,Z system
cis trans isomerism
Cis,Trans Isomerism
  • Cycloalkenes
    • in small-ring cycloalkenes, the configuration of the double bond is cis
    • these rings are not large enough to accommodate a trans double bond
cis trans isomerism18
Cis,Trans Isomerism
  • trans-cyclooctene is the smallest trans cyclooctene that has been prepared in pure form and is stable at room temperature
  • the cis isomer is 38 kJ (9.1 kcal)/mol more stable than the trans isomer
  • the trans isomer is chiral even though it has no chiral center
dienes trienes and polyenes
Dienes, Trienes, and Polyenes
  • For alkenes containing two or more double bonds, change the infix -en- to -adien-, -atrien-, etc.
    • those containing several double bonds are often referred more generally as polyenes
    • following are three dienes
dienes trienes and polyenes20
Dienes, Trienes, and Polyenes
  • for alkenes with n double bonds, each of which can show cis,trans isomerism, 2n stereoisomers are possible
  • example: 22 = 4 cis,trans isomers are possible for 2,4-heptadiene
dienes trienes and polyenes21
Dienes, Trienes, and Polyenes
  • vitamin A, a biologically important compound for which a number of cis,trans isomers is possible
  • there are four double bonds about which cis,trans isomerism is possible, for 24 = 16 stereoisomers
physical properties
Physical Properties
  • Alkenes are nonpolar compounds
  • The only attractive forces between their molecules are dispersion forces
  • The physical properties of alkenes are similar to those of alkanes
terpenes
Terpenes
  • Terpene:a compound whose carbon skeleton can be divided into two or more units identical with the carbon skeleton of isoprene
terpenes24
Terpenes
  • Myrcene, C10H16, a component of bayberry wax and oils of bay and verbena
  • Menthol, from peppermint
terpenes25
Terpenes
  • -Pinene, from turpentine
  • camphor, from the camphor tree
fatty acids
Fatty Acids
  • Animal fats and vegetable oils are both triesters of glycerol, hence the name triglyceride
    • hydrolysis of a triglyceride in aqueous base followed by acidification gives glycerol and three fatty acids
    • fatty acids with no C=C double bonds are called saturated fatty acid
    • those with one or more C=C double bonds are called unsaturated fatty acids
fatty acids27
Fatty Acids
  • the most common fatty acids have an even number of carbons, and between 12 and 20 carbons in an unbranched chain
  • the C=C double bonds in almost all naturally occurring fatty acids have a cis configuration
  • the greater degree of unsaturation, the lower the melting point
  • triglycerides rich in unsaturated fatty acids are generally liquid at room temperature and are called oils
  • triglycerides rich in saturated fatty acids are generally semisolids or solids at room temperature and are called fats
fatty acids28
Fatty Acids
  • the four most abundant fatty acids
fatty acids29
Fatty Acids
  • carbon chains of saturated fatty acids exist largely in the staggered, anti-conformation
  • because of their high degree of order, they pack together well and are held together by dispersion forces
  • as a result both saturated fatty acids and triglycerides derived from them are solids at room temperature
  • following is a saturated triglyceride
fatty acids30
Fatty Acids
  • cis double bonds place kinks in the chains of unsaturated fatty acids
  • unsaturated fatty acids and the triglycerides derived from them do not pack as well in a crystal lattice as their saturated counterparts, and have weaker dispersion forces between their molecules
  • butter fat, for example, has a high content of saturated fatty acids and is a solid at room temperature
  • salad oils (from plant oils) have a high content of polyunsaturated fatty acids and are liquid at room temperature