CHEM24 Dr.

Spence

1. Provide the functional groups, excluding alkanes,presentin eachmolecule:

€thtc &fef/c
r,rldehl/*. QrnrnO krll:v?€.-
cilllnt o

--*'l :tF--*L"lil
H n
>\---^--
l,'t L7-
ri-Y^xt
i l .

L t'l1n \2 rl
o
, iltl
rt\o
$ d ?
I t $ rrY*c, "oAAo,
t.v{ d
alFll otlc,y\no
ettec I
h.rhc,ta, C'acbor.yliu
fhnol
) Forthemolecu1esinquestion1,identifyurr@anda1l1ohydrogen5'-rcka,rrn..rah,&
/ 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,
(b) Which do you think is a more reactive Lewis Acid? Explain. fttr-l'+V-lilt-.
U a 191'-6cvnf
t l It (") frrv.*k'> hcn'rt
Q.T-H R* t"-//tta (e?$.{1q-nct-cq4frV,J huvt [c*nn
A
I tVr\wqpn rrhi"h r,u?*ql'en>+
{"oo V
o(, / tefi(); tt"r"en*C=c) VWJ
I e - ct- - N f l z
R-c-t{ i t7 ) f tnlrlc*r17, €a*tr,,t'g|hcdt ,J**t'T
t
Jz l.rvr:t
?*trn At{sDFfl 1b caf\a'nJl ca{}w'l
t g).
rt ; ur,rtt1}a16ler'un) '#ctcJ
R- C'- N:rlu nn*k,ttj
Describethe relationship betweenthe following pairs of molecules as identical, constitutional
isomers,conformationalisomers,or completelydifferent compounds.

Canfl\-fi-rtuncrl 1,4qir\e\ ,Jo,t\r \\

o
u
dn f Fert..,tt a
l &
-A-t- .y" AoA & /\\,/ w I

onq.l
Co"l,6d rn111,
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'rt-
C= f
-
{) = Z ,i ,} Ln',
"nt\h-[lc,ctr^'nL

6. Draw the skeletal structurefor eachof the following compounds:

3.3-dimethylpentane 1-chl oro -2, 4,4 -trrmethylp entane

I t , /
rL l" i I V
/)i^\ .. r,At.

2-(1,2- dimethylpropyl ) -4-propyl decane 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.

OH O O

H O

alcohol aldehyde ester

O O
Cl Cl
O HO OH

alkyl halide ketone carboxylic acid

O O NH2 O

O 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
O alcohol
alkene

Br
halide
aromatic ring or arene ring
O amine
O NH2

OCH3 OH
H
N ester aldehyde O
H
carboxylic acid
amine
 nitro

O
ketone

O N carboxylic acid
O
N
O
C

nitrile OH

aromatic ring or arene ring

assumed hydrogens given with 3-D perspective
OH OH
H H
H H H H
H H H H
H H
H O O H H H
H H Br H Br
H H H HH H HH
H H H
H
H H H H H H H OR
H OH
H OH
H H
H H H H
H H H
H H
H
H Br H Br
H HH H HH

Stereoisomers
H H H
H H
H
H H
H
H N H O NH2
H
H H HH O OH
H
OR H OCH3 H H O
H
H H H H H OR
H H
H
H
H O NH2
H H
H OH
H N H H
H H H H O

Stereoisomers
Stereoisomers
 O

O N H
O
N O
H C
H
HH HH 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
aromatic tetrahedral alkyne
ring N amine linear

O O trigonal planar
O
ester ketone trigonal planar
alkene

meperidine
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

O Prostaglandin E2

HO sp2
OH
3°
2°
sp3
 sp2
O
N sp3
O
Novocain
1° NH2
amine 1° ester

sp3

4°

Cholesterol

HO 2°
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 C6H14 C5H12 C5H10

A
14. Label the functional groups in the molecules below.

NH2 NH2
Br CH3
H
O
H3C Br O
OH

amine, alcohol, amide alkyl halide alkene, aldehyde

O
O O OH O
HO OCH3 O O

O
carboxylic acid, ketone
alcohol, ester alkene, ether, anhydride
aromatic ring/arene ring

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 butane pentane

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 H 3C

OH
OH
CH3 OH