CHEM24
1.
Dr. Spence
Provide the functional groups, excluding alkanes,presentin eachmolecule:
€thtc
QrnrnO
r,rldehl/*.
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H n
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L
t'l1n
o
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t $
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/
Uo^ io Ccnrhrn
6,r nOr^.,I
Conrrrrttu Y C
Caooct.t Je iC
3.
Considerthe two functional groups,aldehydeand amide, to answerthe following questions:
(a) Which do you think has a shorterC:O bond? Explain (hint, think resonance) Al"b[t/"t,
U
t l
(b) Which do you think is a more reactive Lewis Acid? Explain. fttr-l'+V-lilt-.
a
191'-6cvnf
Q.T-H
It
R* t"-//tta
A
I
o(,
I
R-c-t{
rrhi"h
V
/
e - ct- - N f l z
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r,u?*ql'en>+
tefi(); tt"r"en*C=c) VWJ
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Describethe relationship betweenthe following pairs of molecules as identical, constitutional
isomers,conformationalisomers,or completelydifferent compounds.
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CHEM24
Dr. Spence
Providethe completeIUPAC namefor eachof the following compounds:
{
(r
I -7,\ -J, mrtlrytn':Yrc'vne
fr ' 5' 19abdJ
-f -tnrthylhe6lan(??= 3 - ewrt/ -ttr-tr'"Et"111
-nrethlt^ Lt'{'roftlhtghr'rtC= f
"nt\h-[lc,ctr^'nL
{) = Z ,i ,} Ln',
6.
Draw the skeletal structurefor eachof the following compounds:
3.3-dimethylpentane
/)i^\
2-(1,2- dimethylpropyl ) -4-propyl decane
1-chl oro -2, 4,4 -trrmethylp entane
I
I
rL l" i
..
t , /
V
r,At.
3,4-di ethyl-2 -methylhexane
*+ one of thesenamesis incorrect,which one is it?
tono/-t\ ch'rirr = 12 not lD I
1
Draw the nine constitutionalisomersof CuHre.
l
)
8. The following molecules only have a single functional group. Identify to which class of
organic compounds each molecule belongs based on its functional group.
O
OH
O
O
H
aldehyde
alcohol
ester
O
Cl
O
Cl
HO
O
alkyl halide
O
O
carboxylic acid
ketone
O
OH
O
NH2
O
ester
amine
ether
9. Label the functional groups in the molecules below. For each compound, fill in the assumed
nonbonding electron pairs and the assumed hydrogens. All atoms are neutral unless a charge is
shown. For additional practice, assign the hybridization/geometry for each atom.
ketone
ketone
OH
O
alcohol
O
alkene
Br
halide
aromatic ring or arene ring
amine
O
O
OCH3
N
ester
NH2
OH
H
aldehyde
O
H
carboxylic acid
amine
nitro
O
ketone
O
O
carboxylic acid
N
N
O
C
OH
nitrile
aromatic ring or arene ring
assumed hydrogens given with 3-D perspective
H
H
O
H
O
H
H
H
H
H
H H
H
H H
H H
H
H
H
H H
OH
H
H
H
H
H
HH
H
OH
H
H
H
HH
OH
H
H
H
H
H
Br
H
H
H
O
H N
H
H
H
O
HH
H
H
H
H H H
H
Stereoisomers
NH2
OH
H H
OCH3
H
H
H
H
O
OR
O
H
H N
H
H
H
Br
H
NH2
OH
H
H H
O
Stereoisomers
H
H
HH
Stereoisomers
H H H
OR
H
H
OR
H
H
H
H
H
Br
H
H
H
H
H
H
H
H
H
HH
OH
H
H
H
H
H
H
H
Br
O
O
O
N
O
C
H
H
HH
HH
H
N
OH
H
H
10. Below are shown two common pharmaceuticals: meperidine (Demerol), which is an
analgesic (pain-killer), and norethindrone, a synthetic hormone used in birth control pills.
a. For each, circle and name any functional groups you can identify.
b. For each atom marked with an arrow, determine the local geometry.
c. Determine the molecular formula for each compound.
alcohol
trigonal planar
tetrahedral
OH
alkyne
tetrahedral
aromatic
ring
N
O
O
amine
linear
trigonal planar
O
ester
ketone
meperidine
trigonal planar
alkene
norethindrone
C15H21NO2
C20H26O2
11. For the molecules below, give the information requested by the letter scheme.
a. name these functional groups.
b. give the degree of substitution for these carbons.
c. give the hybridization of these atoms.
carboxylic acid
ketone
O
OH
Prostaglandin E2
O
HO
2°
sp2
OH
3°
sp3
sp2
O
sp3
N
1°
O
amine
1°
Novocain
NH2
ester
sp3
4°
Cholesterol
2°
HO
sp2
alkene
alcohol
12. For the molecules below, determine the number of 1°, 2°, 3°, and 4° substituted carbons.
1° _2_ 2°_7_ 3°_2_
4°_1_
1°_4_ 2°_7_ 3°_2_ 4°_2_
13. For the following compounds below determine which are isomers of each other. What kind of
isomers are they?
There are two sets of constitutional isomers, A and B.
C6H14
C6H12
C6H12
B
A
C6H14
C5H12
C5H10
14. Label the functional groups in the molecules below.
NH2 NH2
Br
O
H3C
OH
amine, alcohol, amide
O
O
HO
CH3
H
Br
O
alkyl halide
alkene, aldehyde
O
OH
O
O
OCH3
O
O
carboxylic acid, ketone
aromatic ring/arene ring
alcohol, ester
alkene, ether, anhydride
15. Name the following compounds using IUPAC nomenclature.
a. 2,5,5-trimethylheptane
b. 5-chloro-3-methyl-4-propyloctane
Cl
16. Name the following compounds using IUPAC nomenclature.
a. 3-methylhexane
b. 2-iodobutane
I
17. The names given for the following structures are wrong. Specify the errors in naming, and
give the correct names.
a. 2,2,5-methylheptane
correct name: 2,2,5-trimethyl-heptane; tri was missing
b. 5-(1-methylpropyl)octane
correct name: 3-methyl-4-propyloctane; parent is chosen to maximize branching/substituents,
and numbering is chosen to give lowest numbers
18. Draw the skeletal (line/angle) formulas for the following.
a. 3-ethyl-5-methyl-4-(1-methylethyl)octane
b. 2-bromo-1-ethyl-3-propylcyclohexane
Br
c. 3-(1-methylcyclopropyl)-4-propylheptane
d. cis-2-ethyl-1,1,3-trimethylcyclopentane
19. Draw the skeletal(line/angle) formulas for the following.
a. 3-ethyl-5-methyloctane
b. 1-bromo-3-isopropylcyclohexane
Br
20. Rank the following compounds from lowest boiling point to highest boiling point. Justify
your answers with brief explanations.
<
propane
<
<
2-methylpropane
pentane
butane
First trend: the larger the molecule (higher molecular weight), the higher the boiling point.
Second trend, for 2-methylpropane vs butane (which are isomers): isomers that are more
spherical have lower boiling points since they have weaker attractive forces between the
molecules. The strength of dispersion forces between molecules depends on how much surface
area is available where they collide; spherical molecules have less surface area for these weak
attractive forces.
21. For each set, identify which compounds are isomers, and indicate what type of isomers they
are.
a. constitutional (structural) isomers
b. constitutional (structural) isomers
OH
OH
CH3
H 3C
OH
OH