山东大学有机化学第八版烯烃和炔烃PPT

Heat of Combustion
CH3 CH3 C C H
CH3CH2CH=CH2
CH3 H C C
H CH3
H
2717 KJ/Mole 2710 KJ/Mole 2707 KJ/Mole
+ 6O 2
4H 2O + 4 CO 2
Alkyl groups stabilize carbon-carbon double bonds
δ δδ δδδ CH3 CH2 CH2
δ δ Y C +I C H I=0 δ δ C X -I
δ Cl
Electron-withdrawing group:
-NO2 > -CN >COOH> -F>-Cl >-Br >-I -I >-OH >-C6H5 >-CH=CH2 >-H
Electron-donating group:
CH3 H C C H H
When speaking of an atom’s ability to polarize a bond, we often use the term inductive effect. An inductive effect: is simply the shifting of electrons in a bond in response to the electronegativity of nearby atoms.
higher
Br F
lower
Zusammen (together)
higher Cl lower
H C=C
lower
F Br
higher
Entegegen (opposite)
Is this E or Z?
Br Cl C=C CH3 H
Is this E or Z?
Br Cl C=C CH3 CH2CH3
Organic Chemistry
for Students of Medicine and Biology 大学化学III和大学化学III（2）
March 18, 2015
Chapter 3 Alkenes and
Alkynes
March 10, 2015
(CnH2n)
Nomenclature Structure Preparation Reactions
7-Fluoro-1, 3, 5-cycloheptatriene
-ene -ol
CH3 CH3CH CHCHCH2CH2OH
3-methyl-4-hexen-1-ol
CH 3 4 5 6 7 8 CH 3 CH 2 CCHCH 2 CH 2 CH 3 CHCH 2 CH 3 3 2 1
பைடு நூலகம்
4-ethyl-5-methyl-3-octene
CH3 CH3 CH CH CH2
3-methyl-1-butene
CH3 CH2 CH2 BrCH2CH2CH2CHCH CH2
6-bromo-3-propyl-1-hexene
CH3
1-Methylcyclohexene
2-methyl-1,3-butadiene
F
6 5 4 3 1 2
Polyethylene
H2 C CH2 H2 C CH2 H2 C CH2
CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -
Samples of polyethylene
Polypropylene
CH 3 CH 2 =CH
CH3 CH3 CH3 CH3 CH3
Rule 2. If a decision can’t be reached by ranking the first atoms in the substituents, look at the second, third, or fourth atoms away from the double-bond carbons until the first difference is found.
E If 2 atoms the same look at next one.
Is this E or Z?
Br Cl C=C CH2OH CH2CH3
Z
Br Cl C=C
CH2OH CH=O
E
count twice
Question: (CH3)3C- and
-CH2Cl, which has the priority?
H CH3 C C H CH3
H CH3
C
C
CH3 H
CIS
TRANS
Stereo View
Cis-2-butene
Trans-2-butene
TRANS
CIS
?
Break pi bond
ROTATION HINDERED
Is this cis or trans?
Cl H C=C Br F
E-Z Nomenclature
CH2-CH-CH2-CH-CH2-CH-CH2-CH-CH2-CH-
What is the name of this compound?
1,3-butadiene
isoprene
CH 3 H2C CH C CH 2
isoprene
Rubber
Vitamine A
OH
VINYL GROUP CH2 CH
*
C C
*
*
C C
*
(Z) (E)
Z-configuration: high-priority group
on the same side of the double bond.
E - Z Cahn-IngoldPrelog Priority Rules SEQUENCE RULE : 1. Assign priority based on atomic number
O- >-COO-> -C(CH3) 3>-CH(CH3) 2> +I -CH2CH3>-CH3>-H
Review
Alkenes Common Names IUPAC Names Structure Bonding
Sequence rules
Cis-Trans isomerism Inductive effect
vinyl chloride CH2 CH Cl PVC, “vinyl”
Allyl Group
CH2 CH CH2 (2-propenyl)
Allyl Alcohol
CH2 CH CH2 OH
Electron Density Map Ethylene
H
o 117.2
H C C H
H
Stereoisomers
ALKENE COMMON NAMES
Ethylene Propylene
H2C
CH2
CH3 CH CH2
CH3
Isobutylene
CH3 C CH2
IUPAC NAMES
CH3 CH3
ethane
H2C CH2
ethene
(1) Find the longest carbon chain that contains the double bond, and name the compound using the suffix-ene. (2) The position of double or triple bond in the base chain must be indicated using the lowest possible numbers. (3) The entire compound is named by first listing the substituents in alphabetical order. Next the position of the double bond is indicated, followed by the name of the parent carbon chain.
H C H H H C NH2 H
Rule3. Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.
H C O R
H O C R O
is equivalent to
higher lower
Cl H C=C
(4) If more than one double bond is present, give the position of each and use one of suffixes –diene, triene, and so on.
What is the name of this compound?
Is this E or Z?
CH3 H C=C H CH2CH3
E or trans
Is this E or Z?
CH3 H C=C CH3 CH2CH3
E or CIS
CH 3 CH 3 CH 2 CH CH 2 CH 2 C CH 3 CH 2 CH 2 C CH 3 H
(E)-6-Methyl-3-propyl-2-octene