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 CHE-300 Organic Chemistry I    Dr. Noel Sturm
office NSM D-323 [phone] or
243-3376 nsturm_at_csudh.edu    office hours by
Appointment
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Web page http//www.nbs.csudh.edu/chemistry/facul
ty/nsturm Print the slides as Hand-Outs, 6 per
page, before coming to class.
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Text   Organic Chemistry, Morrison Boyd
(6th Edition)   Study Guide to..., Morrison
Boyd Supplement...   Model kit  
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Grading No Curve!, Everyone Can Earn An
A A 100-91 A- 90-89 B 88-87 B 86-81 B- 8
0-79 C 78-77 C 76-71 C- 70-69 D 68-67 D
66-60 F 59-0 Weekly Exams No make ups! Begin
at 1000! 
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Daily Homework Required! Final Exam, June 30th,
10-1215, NSM C-221 comprehensive!!  Cheating
Dont do it! The penalties are severe.   Turn
off all cell phones and pagers!
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Organic Chemistry difficult, challenging!
memorization course (NOT! wellmaybe), body of
knowledge application of theory!  How to
succeed? 1. look over the text before
lecture. 2. listen carefully to lectures 3.
participate in quick thinks 4. complete the
work-sheets 3. read the text (take notes) 4.
do the homework (twice...?) 5. review
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Organic Chemistry - the study of the compounds of
carbon, their properties and the changes that
they undergo.   Descriptive approach -
  nomenclature syntheses reactions mechani
sms ...
8
First review topics from gen. chem. important to
o-chem.  atomic structure   subatomic
particles   mass charge protons
neutrons electrons   nucleus protons
neutrons electron shells subshells electrons
1 amu 1
1 amu 0
0 amu - 1
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atomic number number of protons in the nucleus
of the atom (different for each element)
Hydrogen 1, Helium 2, Lithium 3,...   also
the number of electrons in a neutral atom   Iron
26 26 protons 26 26 electrons-26 net
charge 0
10
atomic mass mass of an atom sum of the weights
of the protons neutrons.   But, not all atoms
of a given element are identical. isotopes -
atoms of the same element with different numbers
of neutrons.    
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examples of isotopes  prot. neut. H1 1
0 99.985 H2 1 1 0.015   C12 6
6 98.89 C13 6 7 1.11 C14 6 8
... Cl35 17 18 75.53 Cl37 17
20 24.47   F19 9 10 100
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atomic weight weighted average mass of the
atoms combining weight...   electrons gt energy
shells subshells about the nucleus.   shells
1, 2, 3, 4, ... subshells s, p, d, f   orbitals
region in space where an electron of given
energy is likely to be found no more than two
electrons of opposite spin per orbital (Pauli
exclusion principle).
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maximum number of electrons per
subshell s 2 p
6 d 10 f 14
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order of filling  1s 2s 2p 3s 3p 3d 4s
4p 4d 4f 5s 5p 5d 5f 6s 6p 6d 6f spectral
notation 1s2,2s2,2p6
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Fluorine (at. 9) 9p/9e  1s2,2s2,2p5  Chlorine
(at. 17) 17p/17e   1s2,2s2,2p6,3s2,3p5  Bromine
(at. 35) 35p/35e 1s2,2s2,2p6,3s2,3p6,4s2,3d10
,4p5  Iodine (at. 53) 53p/53e   1s2,2s2,2p6,3s2,3
p6,4s2,3d10,4p6,5s2,4d10,5p5
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valence electrons electrons in the outermost
shell   Fluorine has 7 valence elect.  Chlorine
has 7 valence elect.  Bromine has 7 valence
elect.  Iodine has 7 valence elect.
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  PERIODIC CHART OF THE ELEMENTS   I

VIII ----

---- H

He 1 II
III IV V VI
VII 2 --------
--------------------------
-- Li Be
B C N O F Ne
3 4
5 6 7 8 9 10
--------
------------------------ Na
Mg
Al Si P S Cl Ar 11 12

13 14 15 16 17 18 -----------------
------------------------------------------------
---------------- K Ca Sc Ti V
Cr Mn Fe Co Ni Cu Zn Ga Ge As
Se Br Kr 19 20 21 22 23 24 25
26 27 28 29 30 31 32 33 34 35
36 ----------------------------------
--------------------------------------
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd
Ag Cd In Sn Sb Te I Xe 37
38 39 40 41 42 43 44 45 46 47
48 49 50 51 52 53 54
--------------------------------------
---------------------------------- Cs
Ba La Hf Ta W Re Os Ir Pt Au
Hg Tl Pb Bi Po At Rn 55 56
57 72 73 74 75 76 77 78 79 80
81 82 83 84 85 86 ----------------
------------------------------------------------
-------------------- Fr Ra Ac

87 88 89 104 105

------------------------



--------------------------------------------
-------------------------
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho
Er Tm Yb Lu 58 59
60 61 62 63 64 65 66 67 68 69
70 71
----------------------------------------
---------------- Th
Pa U Np Pu Am Cm Bk Cf Es Fm
Md No Lr 90 91 92
93 94 95 96 97 98 99 100 101 102
103 ----------------------
-----------------------------------------------
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periodic chart of the elements metals
nonmetals families (groups) of elements  alkali
metals (group I) Li,Na,K,... alkaline earths
(group II) Be,Mg,Ca,... halogens (group
VII) F,Cl,Br,I,... noble gases (group VIII or
0) He,Ne,Ar,...  group number valence elec.
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Chemical bonding (classical)   chemical bond
force that holds atoms together in
compounds.   ionic bond between metals
non-metals   covalent bond between non-metals
non-metals      
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definitions   ionic bond a chemical bond formed
by the transfer of valence electrons to achieve
noble gas electron config-urations, resulting in
ions held together by electrostatic
attraction.   covalent bond chemical bond formed
by the sharing of valence electrons to achieve
noble gas electron configurations.
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ionic bond example   sodium chloride  sodium
Na, atomic 11 1s2,2s2,2p6,3s1 neon Ne,
atomic 10 1s2,2s2,2p6 if Na loses 1 elect.
then it will have a noble gas elect. config. like
Ne but will be charged, 1 ( 11p/10e ). gt Na
sodium ion
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chlorine Cl, atomic 17 1s2,2s2,2p6,3s2,3p5 ar
gon Ar, atomic 18 1s2,2s2,2p6,3s2,3p6 if
chlorine can gain an electron it will have a
noble gas electron config. like argon but will be
charged -1 (17p/18e) Cl- sodium chloride
NaCl or NaCl-
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covalent bonds  Lewis Dot representations   H B
e Cl   Ne
C O H2O HOH see homework! review
your gen chem text!  
..
.
.
.
.
..
..
.
.
.
.
.
..
.
..
..
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.. .. ..
.. CO2 OCO OCO N2 NN N?N HC
N HCN H-C?N ..
.. H2CO HCO H-CO
.. H
H
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atomic orbitals s p d
etc.
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hybrid atomic orbitals   s p gt 2
sp hybrids s p p gt 3 sp2 s
p p p gt 4 sp3
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Hybrid atomic orbitals sp linear 180o sp2
trigonal 120o sp3 tetrahedral 109.5o
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VSEPR (valence shell electron pair repulsion)
prediction of hybridization   number of ligands
(X) plus number of unshared pair of valence
electrons (E) equals number of orbitals
needed ? what type of hybrid orbitals are
needed
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..
..
eg. H2O gt HOH or HOH 2 ligands 2 lone
pair 4 orbitals AX2E2  sp3 tetrahedral,
109.5o water is a bent molecule with bond
angles of 105o
..
..
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VSEPR AX2 sp 180o linear AX3 sp2 120o trigo
nal AX2E sp2 120o or bent AX4 sp3 109.5
o tetrahedral AX3E sp3 109.5o or
pyramidal AX2E2 sp3 109.5o or bent
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We can use the VSEPR method to predict the shape
and bond angles for simple covalent
molecules.   SHAPE is important!   review gen
chem text!   Do the homework!!!!!
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  PERIODIC CHART OF THE ELEMENTS   I

VIII ----

---- H

He 1 II
III IV V VI
VII 2 --------
--------------------------
-- Li Be
B C N O F Ne
3 4
5 6 7 8 9 10
--------
------------------------ Na
Mg
Al Si P S Cl Ar 11 12

13 14 15 16 17 18 -----------------
------------------------------------------------
---------------- K Ca Sc Ti V
Cr Mn Fe Co Ni Cu Zn Ga Ge As
Se Br Kr 19 20 21 22 23 24 25
26 27 28 29 30 31 32 33 34 35
36 ----------------------------------
--------------------------------------
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd
Ag Cd In Sn Sb Te I Xe 37
38 39 40 41 42 43 44 45 46 47
48 49 50 51 52 53 54
--------------------------------------
---------------------------------- Cs
Ba La Hf Ta W Re Os Ir Pt Au
Hg Tl Pb Bi Po At Rn 55 56
57 72 73 74 75 76 77 78 79 80
81 82 83 84 85 86 ----------------
------------------------------------------------
-------------------- Fr Ra Ac

87 88 89 104 105

------------------------



--------------------------------------------
-------------------------
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho
Er Tm Yb Lu 58 59
60 61 62 63 64 65 66 67 68 69
70 71
----------------------------------------
---------------- Th
Pa U Np Pu Am Cm Bk Cf Es Fm
Md No Lr 90 91 92
93 94 95 96 97 98 99 100 101 102
103 ----------------------
-----------------------------------------------
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Polarity Covalent bonds are polar when the two
atoms sharing electrons have different
electronegativities. eg. HCl d
d- a charge separation or a dipole gives a
polar bond. .. .. O2 OO
has a non-polar bond
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Representation of dipoles using vectors a)
magnitude length b) direction
positive ? negative A molecule will be non-polar
if the vector sum of the bond dipoles is zero
eg. they cancel one another. A molecule with be
polar if the vector sum of the bond dipoles is
non-zero.
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• Determining polarity of covalent molecules
• Lewis dot structure
• VSEPR ? hybridization ? shape of the molecule
• dipoles for polar bonds
• vector sum of the bond dipoles
• vector sum 0 ? non-polar molecule
• vector sum ? 0 ? polar molecule

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CO2 OCO sp linear vector sum
0 non-polar molecule H2O
.. HOH AX2E2 sp3
tetrahedral (bent) ..

vector sum ? 0 polar molecule!
37
CH3OH Both C O are sp3 hybridized. The bond
dipole vectors do not cancel each other and the
molecule is polar. NB must know shape to
determine polarity!
38
Intermolecular forces. Attractions between
molecules. ionic attractions NaCl- (very
strong) Cl-Na dipole-dipole
attractions HBr BrH hydrogen
bonding ( H attached to N,O,F ) HO----HO
H
H van der Waals (London
forces) BrBr (weak) BrBr
39
intermolecular attractions strongest ionic
attractions dipole-dipole / hydrogen
bonding van der Waals weakest ionic
bonds gt ionic attractions polar covalent gt
dipole-dipole attractions non-polar covalent gt
van der Waals
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Cl2 CO2 H2O CH4 KBr
non-polar covalent gt van der Waals non-polar
covalent gt van der Waals polar covalent gt
dipole-dipole
Hydrogen bonding non-polar covalent gt van der
Waals ionic bonding gt ionic attractions
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bonding gt shape gt polarity gt physical
properties physical properties melting
point boiling point solubility The stronger
the intermolecular forces the higher the mp/bp.
Ionic substances have significantly higher mp/bp
than do covalent substances. note mp/bp also
increase with increasing size.
42
Prediction of mp/bp (relatively high or
low?) Mg(OH)2 CH3OH CH2O CH3CH3
mp bp 350oC -- -94oC 65oC -920C
-21oC -183oC 89oC
ionic gt ionic attractions polar gt
dipole-dipole H-bond polar gt
dipole-dipole non-polar gt van der Waals
43
Solubility like dissolves like water
soluble? must be ionic or highly polar
H-bond (hydrophilic) water insoluble? must be
non-polar or weakly polar (hydrophobic) Most
organic compounds are water insoluble!
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Acids/Bases historic acids from L. acidus
sour sour taste react with metals ? H2
react with bases ? water salts change
litmus ? red react with limestone ?
CO2 examples HCl, H2SO4, HNO3, HClO4
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historic bases - bitter taste soapy
feel react with acids ? water salts change
litmus ? blue examples NaOH, Al(OH)3, K2CO3,
NaHCO3
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Lowry-Brønsted Acid - a substance that donates a
proton (H) in a chemical reaction. Lowry-Brønste
d Base a substance that accepts a proton (H)
in a chemical reaction. CH3MgBr NH3
? CH4 Mg(NH2)Br NaOH
H2SO4 ? H2O NaHSO4
base acid acid base
base acid acid
base
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Lewis Acid a substance that accepts an electron
pair in a chemical reaction to form a covalent
bond. Lewis Base a substance that donates an
electron pair in a chemical reaction to form a
covalent bond.
-
BF3 NH3 ?
F3BNH3 Lewis Lowry-Brønsted
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Rule acid/base reactions must run down
hill. stronger acid/base ? weaker
acid/base H2SO4 H2O ? HSO4-
H3O stronger stronger weaker
weaker acid base
base acid H2O NH3 ?
NH4 OH- weaker weaker
stronger stronger acid
base acid base
(note direction of reactions)
49
Within a period of the periodic chart, acid
strength increases with increasing
electronegativity CH4 lt NH3 lt H2O lt
HF Within a family of elements, acid strength
increases with increasing size HF lt HCl
lt HBr lt HI
50
  PERIODIC CHART OF THE ELEMENTS   I

VIII ----

---- H

He 1 II
III IV V VI
VII 2 --------
--------------------------
-- Li Be
B C N O F Ne
3 4
5 6 7 8 9 10
--------
------------------------ Na
Mg
Al Si P S Cl Ar 11 12

13 14 15 16 17 18 -----------------
------------------------------------------------
---------------- K Ca Sc Ti V
Cr Mn Fe Co Ni Cu Zn Ga Ge As
Se Br Kr 19 20 21 22 23 24 25
26 27 28 29 30 31 32 33 34 35
36 ----------------------------------
--------------------------------------
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd
Ag Cd In Sn Sb Te I Xe 37
38 39 40 41 42 43 44 45 46 47
48 49 50 51 52 53 54
--------------------------------------
---------------------------------- Cs
Ba La Hf Ta W Re Os Ir Pt Au
Hg Tl Pb Bi Po At Rn 55 56
57 72 73 74 75 76 77 78 79 80
81 82 83 84 85 86 ----------------
------------------------------------------------
-------------------- Fr Ra Ac

87 88 89 104 105

------------------------



--------------------------------------------
-------------------------
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho
Er Tm Yb Lu 58 59
60 61 62 63 64 65 66 67 68 69
70 71
----------------------------------------
---------------- Th
Pa U Np Pu Am Cm Bk Cf Es Fm
Md No Lr 90 91 92
93 94 95 96 97 98 99 100 101 102
103 ----------------------
-----------------------------------------------
51
Which is the stronger acid? H2O or
H2S? What is the order of base
strength? F- Cl- Br- I-
oxygen sulfur are in the same family and sulfur
is bigger H2S gt H2O
in the halogen family base strength decreases
with increasing size F- gt
Cl- gt Br- gt I-
52
Will H2O react with NaSH as shown below?
H2O NaSH ? NaOH
H2S Will the following reaction proceed as
shown? HI NaCl ? HCl
NaI
WA
SA no, H2O lt H2S
SA WA yes,
HI gt HCl
53
Isomers - different compounds with the same
molecular formula. example C2H6O CH3CH2OH C
H3OCH3 ethyl alcohol dimethyl ether bp
78oC bp 24oC