CHEM 221/04/02

Fall 2015

Date
Lec.01
Sep. 8

Date
Lec.52
Sep. 10

Sep. 10 Sep. 10

Sep. 15 Sep. 17

Topics

Suggested readings

Suggested problems

3-14, 43-49

Smith 1.40

49-51, 60-64, 69-72

Smith 1.43-1.45, 1.59, 1.60, 1.621.64

Smith 1.69, 1.70, 1.79-1.81,

Sep. 17 Sep. 17

Introduction, Syllabus, octet rule, electron

affinity, ionization
Covalent Bonding, Lewis structure and
Hybridization
Inductive effect, Skeletal and 3D
representations
Formal charge, resonance

Sep. 22 Sep. 24

Acidity and Basicity Alkane: Nomenclature

91-111, 33-41, 124129, 133-134

Sep. 24 Sep. 24

119-124, 153-161

Sep. 29 Oct. 1

27-31, 134-138

Brown 2.17-19, 2.27-29abc, 2.30

Oct. 1

Oct. 1

201-210

Oct. 6

Oct. 8

10

Oct. 8

Oct. 8

11

Oct. 13 Oct. 15

Bruice 3.34bcdef, 3.35-36be, 3.3738abdef

Bruice 3.40, 3.44, 3.46-48a-e,ghi,
3.49bc
Bruice 4.37abc, 4.38ab, 4.41, 4.44,
4.50
Brown 3.12-15 Bruice 4.56

12

Oct. 15 Oct. 15

13

Oct.20

Alkane: Newman projection combustion,

melting points
Isomerism, Functional groups,
Conformational analysis of acyclic
compounds, Newman projection
Conformational analysis of acyclic
compounds Alkene: structure, nomenclature
CIP rules Stability of alkenes: Cis, Trans
isomerism and Substitution
Electrophilic addition: mechanism and
carbocation stability TEST 1
Electrophilic addition: carbocation stability,
regiochemistry and hydration Isomerism
Stereochemistry: Three dimensional
representation, optical activity
Stereochemistry: enantiomer, CIP rules,
Fischer projection
Stereochemistry: diastereoisomers, meso
compounds Rings: Structure, Nomenclature,
Strain and Conformational Isomerism

Smith 1.41,1.42, 1.48-1.53, 1.551.58, 1.66-1.68, 1.85abc

Smith 2.34-39, 2.46, 2.47 2.49a-f,
2.50ab, 2.62-63 Brown 2.20,
2.22abcd, 2.23abcdef, 2.24abcdef,
Brown 2.46-47, 2.49

Oct. 22

15-27, 64-68, 79-82

51-60

210-213, 266-270
214-218, 237-241
244-250, 169-173,
183-188
174-176
176-180, 129-131,
138-140

Brown 3.16-17, 3.19, 3.20, 3.21,

3.22, 3.23,
Brown 2.22e, 2.23gh, 2.24gh 2.3436, 2.39-40, 3.24, 3.25, 3.26, 3.27,
3.29, 3.30

CHEM 221/04/02

Fall 2015

14

Oct. 22 Oct. 22

140-152, 180-183
309-312, 319-320

McMurry 10.17, 10.18, 10.20abde

320-324

McMurry 10.21efg

337-343, 350-354
343-346, 354-357

McMurry 11.26, 11.29, 11.30, 11.33,

11.43, 11.57, 11.58,
McMurry 11.25, 11.28abce, 11.44

347-350, 357-360,
362-364

McMurry 11.27, 11.32, 11.35ab,

11.41-42, 11.55,

364-374

McMurry 11.31acd, 11.36-40ab,

11.50-53, 11.60

250-260

Bruice 4.37d, 4.42-43, 4.49, 4.58,

4.60

Nov 17 Nov 19
Nov 19 Nov 19

Rings: Conformational Isomerism

Alkyl halides: structure, nomenclature,and
preparation
Alkyl halides: organometallic reagents
Thermodynamics and Kinetics applied on
electrophilic addition
Substitution reaction: mechanism,
intermediates, stereospecificity
Substitution reactions: transition states and
steric hindrance, effect of nucleophile
Substitution reactions: effect of leaving
group and solvent Elimination reactions:
mechanism, intermediates TEST 2
Elimination: transition state, stereospecificity
and regioselectivity Elimination vs
Substitution
Alkene: Hydration, rearrangement,
Halogenation, hydrobromination and
oxymercuration
Alkene: Stereospecificity, Hydroboration
Alkene: Hydrogenation, oxidative cleavage.

15

Oct. 27 Oct. 29

16

Oct. 29 Oct. 29

17

Nov. 3

Nov. 5

18

Nov. 5

Nov. 5

19

Nov 10 Nov 12

20

Nov 12 Nov 12

21
22
23

Nov 24 Nov 26

Alkyne: structure, nomenclature, addition.

279-293

24

Nov 26 Nov 26

293-303

25

Dec. 1

Dec. 3

26

Dec. 3

Dec. 3

Alkyne: hydrogenation, Acidity, alkylation

and synthesis Lab exam
Radical halogenation : thermodynamics,
mechanism, regioselectivity
Alkene: radical hydrobromination. Synthesis

262-266
266-272

389-414
414-416

Bruice 4.39a,c,d,f-k,m, 4.46, 4.47a,df,h, 4.48a-e, 4.57ab

Bruice 6.24-25a-d,f,i-l, 6.26-27bcef,
6.29acd, 6.30, 6.34ace, 6.39abdef
Bruice 6.28, 6.32-33, 6.36-38a2,
6.41-42, 6.44-6.47, 6.49-50
Solomons 10.21, 10.22, 10.23,
10.24a, 10.25a, 10.27,
Solomons 10.32a,c-g, 10.33abce