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Transcript 
Chapter 5
Alkenes Structure, Nomenclature, and an introduc1on to Reac1vity • Thermodynamics and Kine1cs Paula Yurkanis Bruice
University of California,
Santa Barbara
© 2014 Pearson Education, Inc.
Molecular Formula and the
Degree of Unsaturation
molecular formula = CnH2n+2 – 2 hydrogens for every π bond or ring
degree of unsaturation = the total numbers of π bonds and rings
© 2014 Pearson Education, Inc.
Compounds with Molecular Formula = C8H14
CnH2n+2 =
C8H18
Therefore, C8H14 has two degrees of unsaturation.
compounds with six hydrogens and two degrees of unsaturation
© 2014 Pearson Education, Inc.
Saturated and
Unsaturated Hydrocarbons
Saturated hydrocarbons have no double bonds.
Unsaturated hydrocarbons have one or more double bonds.
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
Replace ane of alkane with ene.
The functional group gets the lowest possible number.
© 2014 Pearson Education, Inc.
Stereoisomers are Named Using
a cis or trans Prefix
© 2014 Pearson Education, Inc.
Nomenclature of Dienes
two double bonds = diene
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
Number in the direction so that the functional group
gets the lowest number.
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
Substituents are stated in alphabetical order.
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
© 2014 Pearson Education, Inc.
Nomenclature of Cyclic Alkenes
A number is not needed to denote the position of the functional group;
it is always between C1 and C2.
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
© 2014 Pearson Education, Inc.
Nomenclature of Alkenes
© 2014 Pearson Education, Inc.
Vinylic and Allylic Carbons
vinylic carbon: the sp2 carbon of an alkene
© 2014 Pearson Education, Inc.
allylic carbon: a carbon adjacent to a vinylic carbon
Double Bonds Have
Restricted Rotation
Rotation about a double bond breaks the π bond.
© 2014 Pearson Education, Inc.
Six Atoms of an Alkene are in the
Same Plane
© 2014 Pearson Education, Inc.
Alkenes Have Cis–Trans Isomers
cis
trans
Cis: The hydrogens are on the same side of the ring.
Trans: The hydrogens are on opposite sides of the ring.
They have different configurations; they can be separated.
© 2014 Pearson Education, Inc.
Which Is Cis and Which Is Trans?
© 2014 Pearson Education, Inc.
The E,Z System of Nomenclature
Z = Zusammen (together)
© 2014 Pearson Education, Inc.
E = Entgegen (opposite)
Relative Priorities
The relative priorities of the two groups depends on the
atomic numbers of the atoms attached to the sp2 carbon.
© 2014 Pearson Education, Inc.
The E and Z Isomers
© 2014 Pearson Education, Inc.
E and Z
© 2014 Pearson Education, Inc.
E and Z
© 2014 Pearson Education, Inc.
Isomers for Compounds with
Two Double Bonds
© 2014 Pearson Education, Inc.
Reactions of Organic Compounds
Organic compounds can be divided into families.
All members of a family react in the same way.
The family a compound belongs to depends on its functional group.
© 2014 Pearson Education, Inc.
Each Family Can Be Put in One
of Four Groups
The families in a group react in similar ways.
© 2014 Pearson Education, Inc.
Electrophiles
An electrophile has
a positive charge,
a partial positive charge,
or an incomplete octet.
© 2014 Pearson Education, Inc.
Nucleophiles
A nucleophile has
a negative charge
or a lone pair.
© 2014 Pearson Education, Inc.
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