C341/ Chapter 1: General Chemistry Review sheet
1.
For   the   condensed   formula   below,   perform   the   following   functions:   a.
Draw   the   correct   Lewis   structures   and   fill   in   the   correct   number   of   lone   pairs   and/or   double   bonds.
b.
Determine   the   molecular   shape   around   each   non ‐ hydrogen   atom.
(tetrahedral,   bent,   etc.)
c.
Determine   ideal   bond   angles   and   identify   any   distortions   from   ideal   bond   angles.
d.
Provide   an   orbital   hybridization   description   for   any   atom   and   be   able   to   describe   the   bonds   in   terms   of   overlapping   atomic   orbitals   (sigma,   pi,   etc.).
In   what   types   of   orbitals   do   lone   pairs   reside?
f.
Which   molecules   are   polar?
Which   molecules   would   be   soluble   in   polar   solvents?
Draw   in   the  δ +   and  δ‐  signs   for   the   polar   bonds.
g.
Finally,   draw   the   correct   lines   structures   for   these   compounds   and   identify   the   functional   groups   in   each.
CH
3
NHCH
3
CH
3
COCH
3
CH
3
CONHCH
2
CH
3
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CH
2
CHCOCH
3
C341/ Chapter 1: General Chemistry Review sheet
(CH
3
)CHC(CH
3
)
2
(no   polar   bonds   below)
CHCCH
2
CH
2
COOCH
3
(not   all   bonds   are   described   because   they   are   SO   similar   to   previous   molecules)
C(sp
2
) -- O(sp
3
) overlap sp
2
, trigonal planar, 120 o
C(sp) -- C(sp
3
) overlap sp
3
, bent, <109.5
o
H H O H H H O H
H H C C C C C O C sp, linear, <180 o
H H H sp
3
, tetrahedral, 109.5
o
H H C C C C C O C
H H
C(sp
3
) -- H(s) overlap
σ
: C(sp) -- C(sp) overlap
π( x
)
: C(2p) -- C(2p) overlap
π( y
)
: C(2p) -- C(2p) overlap
H
O
O
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C341/ Chapter 1: General Chemistry Review sheet
2.
Identifying   conjugation .
The   first   step   to   being   able   to   draw   resonance   structures   is   to   identify   conjugated   atoms.
On   the   structure   of   capsaicin   below   circle   all   of   the   conjugated   atoms.
Capsaicin   is   the   active   component   to   chili   peppers.
The   spicy   flavor   of   capsaicin   comes   from   its   interaction   with   olfactory   and   other   receptors.
The   strength   of   the   interaction   is   controlled   by   a   variety   of   factors,   including   electrostatic   interactions,   which   might   arise   from   uneven   electron   distribution   in   the   capsaicin   molecule.
Resonance   influences   this   electron   distribution.
3.
Practicing   resonance .
The   protein   content   of   a   food   sample   is   estimated   by   determining   its   nitrogen   content.
The   apparent   protein   content   of   some   wheat   gluten   was   boosted   by   the   addition   of   melamine.
While   melamine   is   rich   in   nitrogen,   it   causes   kidney   failure   if   the   amount   is   high   enough.
Polymerization   of   melamine   with   formaldehyde
(H
2
C=O)   gives   melamine   resin,   a   tough   plastic   used   in   kitchen   countertops   and   bowls.
Using   curved   arrows,   provide   two   more   resonance   structures   for   melamine.
4.
Utilize   arrows   properly   to   show   the   formation   of   all   other   resonance   structures   if   they   exist.
Circle   the
most   stable   resonance   structure   for   each   below.
a.
All   resonance   structures   are   completely   equivalent.
Positive   sign   is   on   2 o   carbon   in   all   instances   and   all   have
the   same   number   of   bonds.
b.
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c.
d.
C341/ Chapter 1: General Chemistry Review sheet
e.
f.
5.
Determine   the   functional   groups   below.
Explain   why   the   first   two   compounds   which   have   the   same   molecular   formula,   C
4
H
10
O,   have   such   different   boiling   points.
How   would   you   expect   2 ‐ butanone   boiling   point   to   compare   to   these   relatively?
Discuss   their   order   of   solubility   in   water.
Compound   O
Boiling
Water
Point
Functional
Group
Intermolecular
Solubility
Forces   present
108   o
C
1 o
alcohol
LF,   DD,   HB
Most   soluble   due   to
HBA   and   HBD
34.6
ether
LF,
Least and   o
DD
C
(but   minor) soluble least   DD
due
to   HBA
80   ketone
LF,   o
C
DD
HBA   diethyl
and
(more
higher ether
significant)
DD
than
Boiling   point :   Doing   this   worksheet,   you   can   always   look   up   the   boiling   point   for   2 ‐ butanone   online   with   a   quick   Google   search   –   that’s   not   the   point   of   this   question.
On   an   exam   or   quiz,   you   want   to   be   able   to   deduce   which   compound   has   the   most   and   least   number   of   intermolecular   forces.
The   more   intermolecular   forces,   or   attractive   forces   between   each   other,   it   has   then   the   higher   its   physical   properties   like   boiling   point.
By   understanding   this   concept,   you   should   understand   that   the   ketone   will   have   the   intermediary   boiling   point   because   it   has   intermediary   intermolecular   forces.
Both   the   ether   and   the   ketone   have   DD   forces,   BUT   the   ether   has   two   polar   bonds   that   help   cancel   each   other   out   better   due   to   the   bond   angles   it   experiences   around   the   oxygen   that   is   sp
3
and   109.5
bond   angle.
Water   solubility :   If   a   molecule   has   more   heteroatoms   (F,   N   and   O)   it   can   hydrogen   bond   with   water   more   effectively   and   will   have   higher   water   solubility.
All   three   molecules   have   one   oxygen,   so   this   concept   will   not   be   the   deciding   factor   in   the   choice.
Only   the   alcohol   has   a   HBD   and   HBA   to   bond   with   water.
The   ketone   and   ether   only   have   HBA   and   these   two   molecules   will   not   hydrogen   bond   as   effectively   with   water,   hence,   lower   water   solubility.
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C341/ Chapter 1: General Chemistry Review sheet
6.
Draw   line carbons
as drawings
primary,
for   all   isomers secondary
and of
molecular tertiary.
If
formula you   drew
C
4 an
H
10
O.
Identify   the   functional   groups   and   discuss   the
alcohol,   is   it   a   1 o
,   2 o
,   or   3 o
?
I   may   be   missing   some   isomers   ,   but   you   get   the   point.
7.
Write   the   Lewis   structures   and   condensed   structural   formulas   for   all   isomers   of   molecular   formula   C
4
H
8
O.
Identify   the   functional   groups   and   discuss   the   carbons   as   primary,   secondary   and   tertiary.
O
O
O ether ether 2 o alcohol
OH
3 o
OH alcohol O ketone O alkene + 1 o
OH alcohol alkene + 1 o
OH alcohol aldehyde
H
H aldehyde alkene + 1 o
OH alcohol
OH alkene + 2 o alcohol
OH alkene + 1 o alcohol alkene + 2 o
OH alcohol
O O
O ethers + alkene
8.
Fill   in   the   lone   pairs   on   all   heteroatoms   in   each   compound   and   assign   correct   formal   charges.
O
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C341/ Chapter 1: General Chemistry Review sheet
9.
Identify   as   many   functional   groups   as   possible   and   then   list   the   intermolecular   forces   (LF,   DD,   HBA,   HBD)   found   in   each   of   the   following   molecules.
What   is   the   five   carbon   rule?
Predict   whether   the   following   molecules   would   be   soluble   in   water.
Aspirin ( water soluble, LF, DD, HBA, HBD )
Vitamin C ( water soluble, LF, DD, HBA, HBD )
Melatonin ( water soluble, LF, DD, HBA, HBD alcohol, specifically called an aryl alcohol
HO arene alkane or hydrocarbon
O ether
Vitamin E (fat soluble, primarily LF)
)
Vitamin B
6
( water soluble, LF, DD, HBA, HBD )
alkane alkenes
HO secondary alcohol
Vitamin D (fat soluble, primarily LF, but does have minimal DD and HBA, HBD)
Dimitone ( water soluble, LF, DD, HBA, HBD )
N amine alkene
O carboxylic acid
OH
NH
2 primary amine corrected 1/20/10
Sabril   –   seizure   medication
( water soluble, LF, DD, HBA, HBD )
Cl arene amide
aryl halide
Claritin   –   treats   seasonal   allergies
( fat soluble, LF, DD, HBA )
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N
O
O ester