Pham – Chem 30A – Spring ‘26
Due April 10th (Week 2)
Problem Set #1
(Note: You will need to know how to draw and interpret bond-line structures before attempting this)
006583333revama
I) Draw the Lewis structure of each molecule. Then, using VSEPR theory, draw the 3D bond-
line structure of each molecule, indicating its molecular geometry and orbital hybridization of the
central atom. Use an arrow to indicate the molecular dipole moment, if any. An example is provided
for you.
Ex. 2-chloro-2-methylpropane (t-butyl chloride) a) Methanal (formaldehyde; CH2O)
4
c anterior
H6
0
2
1
left
frac
right
hybridization
mercuin
spa
0
delta seeming
planar
trigonal
Contencio
C
delta tensizedipole
moment
H H pointed aboctenoeband
toward
amoredication
b) Dimethyl ether (CH3OCH3); Central atom = O
spsbancarbonanexam
c) Hydroxylamine (NH2OH); Central atom = N
sps
left
G
H
C
4
81
right
hybridization
H
N
6
0
4
3
5
e1r
molecular tetrahedral
geometry atcaroens atwar
left
end
pyramidal
hline
right
trigonal
6
02 array
begin
molecular
geometry
frac bonoatoxygen
lone
because
bentat 0
pairs
H H
O
H
C ldots
8 f
delta 8 0 H
Hs N
st8
soso
s.I
8overall
That
O
N
H
8
ldots
delta
t
delta dipole
1t H
H t
delta delta
net
dipole
delta s t
I
5 points
toward0 H
uptoexyser
II) Draw bond-line structures for the following molecules:
a) CH3CH2CH2CH2C≡CCH2NH2 b) 2-chloro-2-iodobutane c) Any molecule containing
E isx̅
leftharpoondown
a ketone and a carboxylic acid
total mainchain7 triple
carbonsin bendareus
zigzag
cavenbaton
in
a
more
croons arowwsingu
viate
set
g rums on
bones
carbon iodine also
convene
ketone
R0
end
begin
matrix
carboxylic
R
0
Z 1 sosuoridization a
i on
equiv
6
5 mensei
H
N
2 zag i
spconsut line final
motene
alltetrahedral
aoverall
except
Io
manure
the whichis
triple H
liner
Nik
N
1
, Problem Set #1
III) Using IUPAC conventions, name the following molecules. (Common names accepted)
a)
c
ccc1.3
cc
Name: ________________________________________________
dimethyl Ipentane
c.isopropyl.metali1
b) Name: ________________________________________________
3
bromo isopropyl
cyclopentanesmetmil1,6
c) Name: ________________________________________________
IV) General Knowledge – Answer these general questions about these popular
medicinal drugs by referring to each structure provided.
dicyclopropythexanefunctional
Lenalidomide (Trade name: Revlimid), used to treat multiple myeloma (cancer of plasma cells)
a) What is the name of this functional group?
groupamide lambda
N K
b) What is the hybridization of this nitrogen?
onepairmust C
R
Nitrogen spa beinpbecause
itneeds topartakein
resonance
c) Is the lone pair on this nitrogen delocalized (i.e. can 0
this nitrogen participate in resonance)?
yesbecause it
canparticipatein
Codeine, an opiate typically used as a painkiller
resonanceC
d) What is the name of this functional group?
Is it 1o, 2o, or 3o?
OHfunctional
alcohol
group ddots
Thisaleanelis20
became toitisbondedtotwoourcarvers
attached
c arbon
C
e) What is the hybridization of this oxygen?
cannotpartake
in resonance.coxygen
electron
domainsHi spscc4
f) What is the molecular geometry of this carbon?
cmacular
geemers tetrahedral
2
, Problem Set #1
V) Resonance Structures
a) On the molecule below, circle each atom that contains a p-orbital.
i) How many atoms contain a p-orbital? ______
4z7
atoms6ss
ii) What is the hybridization of the nitrogen atom? _____
p
2
b) Draw 3 more major contributing resonance structures for this molecule. Of the 4, circle the
most contributing structure and draw curved arrows (showing electron movement) that lead
to that structure from the one provided below. Then explain why that is the most contributing
structure. i16
i)
N
H
ii) iii)
ell
leftharpoondown
N i
H H
Theresonancestructure inbox iii isthemostcontributingbecauseit minimizesthetotalamount
offormalcourses i.eoxygenholds theoverallnegateformalchaseon itsthemostelectronegativeatomsAdditionally everyoctet
is runwhich isimportantforresonancestructurestabilityHoweverthemostprominentreasonwhythisstructureis themost
andmostcontributingisaccusethe
stable molecules
overallnegatechaseis on theelectronegativeoxygenasnot
structureshmfulloctetsteeso look
carbonmainly wearour we towardsformalchaseelectronesangruns
VI) Bond-line Mistakes – Below are common mistakes made when using bond-line structures.
Draw the corrected structures.
H H cunner
tipleand has drawis
l
1C
a) tobelinear b)H
C C H
H H H
H
H H
N
3
Due April 10th (Week 2)
Problem Set #1
(Note: You will need to know how to draw and interpret bond-line structures before attempting this)
006583333revama
I) Draw the Lewis structure of each molecule. Then, using VSEPR theory, draw the 3D bond-
line structure of each molecule, indicating its molecular geometry and orbital hybridization of the
central atom. Use an arrow to indicate the molecular dipole moment, if any. An example is provided
for you.
Ex. 2-chloro-2-methylpropane (t-butyl chloride) a) Methanal (formaldehyde; CH2O)
4
c anterior
H6
0
2
1
left
frac
right
hybridization
mercuin
spa
0
delta seeming
planar
trigonal
Contencio
C
delta tensizedipole
moment
H H pointed aboctenoeband
toward
amoredication
b) Dimethyl ether (CH3OCH3); Central atom = O
spsbancarbonanexam
c) Hydroxylamine (NH2OH); Central atom = N
sps
left
G
H
C
4
81
right
hybridization
H
N
6
0
4
3
5
e1r
molecular tetrahedral
geometry atcaroens atwar
left
end
pyramidal
hline
right
trigonal
6
02 array
begin
molecular
geometry
frac bonoatoxygen
lone
because
bentat 0
pairs
H H
O
H
C ldots
8 f
delta 8 0 H
Hs N
st8
soso
s.I
8overall
That
O
N
H
8
ldots
delta
t
delta dipole
1t H
H t
delta delta
net
dipole
delta s t
I
5 points
toward0 H
uptoexyser
II) Draw bond-line structures for the following molecules:
a) CH3CH2CH2CH2C≡CCH2NH2 b) 2-chloro-2-iodobutane c) Any molecule containing
E isx̅
leftharpoondown
a ketone and a carboxylic acid
total mainchain7 triple
carbonsin bendareus
zigzag
cavenbaton
in
a
more
croons arowwsingu
viate
set
g rums on
bones
carbon iodine also
convene
ketone
R0
end
begin
matrix
carboxylic
R
0
Z 1 sosuoridization a
i on
equiv
6
5 mensei
H
N
2 zag i
spconsut line final
motene
alltetrahedral
aoverall
except
Io
manure
the whichis
triple H
liner
Nik
N
1
, Problem Set #1
III) Using IUPAC conventions, name the following molecules. (Common names accepted)
a)
c
ccc1.3
cc
Name: ________________________________________________
dimethyl Ipentane
c.isopropyl.metali1
b) Name: ________________________________________________
3
bromo isopropyl
cyclopentanesmetmil1,6
c) Name: ________________________________________________
IV) General Knowledge – Answer these general questions about these popular
medicinal drugs by referring to each structure provided.
dicyclopropythexanefunctional
Lenalidomide (Trade name: Revlimid), used to treat multiple myeloma (cancer of plasma cells)
a) What is the name of this functional group?
groupamide lambda
N K
b) What is the hybridization of this nitrogen?
onepairmust C
R
Nitrogen spa beinpbecause
itneeds topartakein
resonance
c) Is the lone pair on this nitrogen delocalized (i.e. can 0
this nitrogen participate in resonance)?
yesbecause it
canparticipatein
Codeine, an opiate typically used as a painkiller
resonanceC
d) What is the name of this functional group?
Is it 1o, 2o, or 3o?
OHfunctional
alcohol
group ddots
Thisaleanelis20
became toitisbondedtotwoourcarvers
attached
c arbon
C
e) What is the hybridization of this oxygen?
cannotpartake
in resonance.coxygen
electron
domainsHi spscc4
f) What is the molecular geometry of this carbon?
cmacular
geemers tetrahedral
2
, Problem Set #1
V) Resonance Structures
a) On the molecule below, circle each atom that contains a p-orbital.
i) How many atoms contain a p-orbital? ______
4z7
atoms6ss
ii) What is the hybridization of the nitrogen atom? _____
p
2
b) Draw 3 more major contributing resonance structures for this molecule. Of the 4, circle the
most contributing structure and draw curved arrows (showing electron movement) that lead
to that structure from the one provided below. Then explain why that is the most contributing
structure. i16
i)
N
H
ii) iii)
ell
leftharpoondown
N i
H H
Theresonancestructure inbox iii isthemostcontributingbecauseit minimizesthetotalamount
offormalcourses i.eoxygenholds theoverallnegateformalchaseon itsthemostelectronegativeatomsAdditionally everyoctet
is runwhich isimportantforresonancestructurestabilityHoweverthemostprominentreasonwhythisstructureis themost
andmostcontributingisaccusethe
stable molecules
overallnegatechaseis on theelectronegativeoxygenasnot
structureshmfulloctetsteeso look
carbonmainly wearour we towardsformalchaseelectronesangruns
VI) Bond-line Mistakes – Below are common mistakes made when using bond-line structures.
Draw the corrected structures.
H H cunner
tipleand has drawis
l
1C
a) tobelinear b)H
C C H
H H H
H
H H
N
3
