1. A Review of “Organic Chemistry” Some Important Concepts and Structure
in First Term
Part A
Some Important Concepts and Structure
1. Different kinds of Organic Compounds.
Alkanes
Cycloalkanes
Alkyl halides
Alcohols
Saturated
Compd.
Hybrization
Geometric
structure
C atoms
Alkenes
Alkynes
Diene
Arenes
Unsaturated
Compd.
Alkyl
Allylic
Benzyl
Reactive
intermediates
Carbocations
Radicals

2. 2. Formation of Chemical bonds.
Stereoisomers
Configurational
isomers
Enatiomers(R,S)
Diatereomers
Meso-isomers
Racemic mixture
C–C σbond
C–Hσbond
C=C double bonds
cis-trans
Isomers:
(Z),(E)
Triple bonds
Structure
Chiral
Achiral
Optical
activity
Reso-
nace
form
Optical
Mole.
Symetric
Unsymetric
3. Bilingual nomenclature.
Symetric
elements
Constitutional
Stereoisomers
Conformers
4. Isomers
Newman
Fischer
Projections
5. Aromaticity
Chair conformation

3. 6. Organic acids and bases
7. Substitutent effects
Problem 1
The structure of Comp. A is represented
by the constitution shown:
(a) How many of the optical isomers?
(b) Write the Fischer projections of
the optical isomers and give the IUPAC
names.
(c) Sight down the C3–C4 bond, and draw
the most stable Newman projection
formulas of the optical isomers .
(d) Identify the relationship of these optical
isomers.

4. Problem 2
Write a structural formula for the most
stable conformation of the each of
the following compounds:
(a) cis-Cyclohexadiol.
(b) trans-4-tert-Butyl-1-methylcyclohexane.
(c)
Give the stable
conformer.

5. Part B. Organic Reactions
Halogenation of alkanes.
α- Halogenation of alkenes.
Reactions of NBS.
Radical
Reactions
d. Anti-Markovnikov addition:
(HBr–ROOR)
Substrates Nucleophile
a. Alkyl halides
2. Nucleophilic
Substitutions
b. Alcohols:
HX, PX3, SOCl2
I -
TSCl or MsCl
ROTs

6. Friedel-Crafts reactions
3. Elimination
Substrates Electrophiles
HX, X2, X2+H2O,
H+/H2O
(HgSO4/H2SO4/H2O)
B2H6/H2O2–OH -,
Alkenes
Alkynes
4. Electrophilic
additons
1,2-adddition
1,4-addition
cycloaddition
Conjugated
dienes
5. Aromatic
Electrophilic
substitutions
Halogenation
Nitration
Sufonation
Friedel-Crafts reactions

7. Alkenes Dienes Alkanes Carboxyl Acids Benzoic acid
H2 / Pd,Ni…
Alkenes
Dienes
Alkanes
6. Hydrogenations H2
Pd,Ni… H2
Lindlar-Pd
or P-2 Catalyst
cis-Alkenes
Alkynes
Na or Li
Liq. NH3
trans-Alkenes
Alkenes
Aldehydes
or Ketones
7. Oxidations
Alkynes
Carboxyl
Acids
Benzoic
acid
Alkylbenzens:
Na2Cr2O7/H+

8. Aromatic Electrophilic
Part C. Organic Synthesis
The transformation of
functional groups
Organic Synthesis
b. The change of C skeleton
c. The shift of functional
groups
Part D. Mechanism of Organic Reactions
SN1 Reactions
E1 Reactions
Rearrange-
ment
The formation of
a carbocation
Addition of HX
to alkenes
Aromatic Electrophilic
substitution
b. The halonium ion:
Addition of X2 to a alkene

9. c. Bimolecular Reactions
SN2 Reactions
E2 Reactions
Transition States
Table 1 Over summary of SN1,SN2,
E1 and E2 reactions
RCH2X
CH3X
R2CHX
R3CX
Methyl ° ° °
Bimolecular reactionly SN1/E1 or E2
In solvolysis give
SN1/E1,and at low
temperature SN1
is favored and gaves
mainly E2
with stronger
bases(e.g.,RO -)
Gaves mainly SN2,
with weak base
(e.g.,I-,CN -,
N3-,RCO2-)
and mainly E2
With stronger
bases(e.g.,RO -)
Gaves mainly SN2,
except with a hind-
ered-strong base
[e.g.,(CH3)3CO-]
and then gives
mainly E2
Gives
SN2
reac-
tions

10. Part E. Stereoselectivity of Reactions
1. Catalytic hydrogenations of alkynes:
H2 / Lindlar-Pd
Syn-addition
P-2 catalyst
Anti-addition
Li or Na / Liq. NH3:
2. Addition of X2 to Alkenes:
Anti-addition
3. Hydroboration-Oxidation of alkenes:
Syn-addition
Syn-addition
4. Epoxidation of Alkenes:
Inversion of configuration
5. SN2 Reactions:
Retention of configuration
SN1 reaction:
racemization
6. E2 Reaction:
Anti-Elimination

11. Part F. Regioselectivity of Reactions
1. Electrophilic addiitons of alkenes:
Markovnikov’s rule
2. Addition of HBr to a alkene in the
presence of ROOR:
Anti-Markovnikov’s rule
3. Elimination:
Zaitsev’s rule
4. Aromatic electrophilic substitution
of substituted benzenes:
Directing effect of substituents
on aromatic ring

12. Part G. Identification of Organic Compounds
1. Ozonolysis of alkenes and alkynes.
2. Oxidations of Alkenes by KMnO4.
3. Additions of Br2 to Alkenes.
4. Reactions of Terminal alkynes with
Ag(NH3)NO3 or Cu(NH3)Cl.
5. Reactions of conjugated dienes with
maleic anhydride.
6. Oxidations of alkylbenzenes to benzoic acid ……

13. 1. 2.
Isobutyl iodide tert-Butyl chloride

14. 3. Racemization SN2 Reaction (R)-sec-Butyl alcohol (S)-sec-Butyl azide
(R) (R)-

15. 1-Bromo-2-ethylpentane
Problems to Chapter 8
P246
7.22 (d)
1-Bromo-2-ethylpentane
2- 乙基-1-溴戊烷
3-Bromomethylhexane
7.29 (a) SN2
Rate
<
p-π conjugation
Electronic effect
(c) also.

16. 7.30
(c)
(f)
7.32
SN1:
Steric
hindrance
SN2:
crowding

17. 7.34
(a)
SN2
(b)
(c)

18. 7.35
Ch.P196
SN1
Inversion
Retention
Racemic-forms

19. 7.48
(a) E1
(b)
SN1
7.49 E2

20. 7.50
(Z)-2,3-Diphenyl-2-butene
7.51
(a)
(b)

21. 7.52 7.53(E) 7.55 SN1 (2R,3S)-2-Bromo-3-phenylbutane
(Z)-2-Phenyl-2-butene
7.53(E)
7.55
SN1

22. You should comprehend well the meaning of the following reactions :
7.58 A
You should comprehend well the meaning
of the following reactions :
1.Hydroboration-Oxidation of alkenes.
2. Diels-Alder Cycloaddition Reaction.
3. Friedel-Crafts Alkylation of Arene.
4．SN2 Reaction.
5．The Williamson Synthesis of Ethers.