1

Chapter 4
Definitions:
Alkanes
Alkenes
Alkynes
Cycloalkanes
Cracking(thermal and catalytic)
Polymerization
Constitutional Isomers
Haloalkanes
Alcohols
Cyclics
Bicyclo
Homologs/homologous series
Solubility
Acetylenic hydrogen/alkynide ion/acetylide ion
Conformations/Conformational Analysis
Newman Projections
Eclipsed/Staggered/Gauche/Anti
Chirality
Stereochemistry
Ring Strain
Angle/Torsional Strain
Chair/Boat
Catenanes
Pheromones
Paraffins
Alkylation
Retrosynthesis

1. Oil Refining/Fractional Distillation

Petroleum
source of alkanes
types of alkanes
Petroleum refining
fractional distillation
catalytic/thermal crackinGg
polymerization

2. Alkane structure
molecular formula/structural formula/condensed formula
line formula(zig-zag)
geometry
alkyl substituents
isopropyl
isobutyl
sec-butyl
tert-butyl
neo-pentyl
3. Nomenclature
A. Alkanes--chart p. 136(table 4.4)
B. IUPAC rules/common names
1. Locate longest continuous chain. Name it according to p. 136.
a. if 2 chains have equal length. The chain with most substituents
becomes the parent chain.
2. Number the chain
a. if only one substituent, number to get to that substituent first
b. if two substituents, number from side that first gets to a
substituent
c. if both substituents are equal distant from both sides and
both are alkyl, use alphabet to determine the numbering
d. if both substituents are equal go to next carbon with a
substituent. Number from side that gives smaller total.
I.E. 2,4 is better than 2,5
e. halides have same priority as alkyls. Use alphabet to determine
priority.

f. alcohols have highest priority. If an alcohol is present number

the chain to get to the alcohol first regarldless of alkyl and halide
groups. Alcohols also take priority over alkenes and alkyenes.
g. ethers have same priority as alkyls. Use alphabet to determine
priority
h. alkenes and alkynes are used to determine priority if there are
no alcohols present in a molecule
3. Give each substituent a number and a name(3-bromo, 2-methyl)
a. if two groups are on the same carbon it must be numbered twice
i.e 2,2-dimethyl
4. Common substituents can be grouped together(2-methyl, 3-methyl can
be called 2,3-dimethyl).
5. Numbers are separated by commas. Numbers and letters are
separated by dashes.
6. Prefixes
a. alkyl substituents are named alphabetically in the front(di, tri,
sec,do not count for alphabetical, dimethyl comes after ethyl)
b. Halides are named alphabetically in the front
1.
2.
3.
4.

Iiodo
Brbromo
Clchloro
FFluoro

c. ethers are named alphabetically in the front

1. methyl ethermethoxy
2. ethyl etherethoxy
3. propyl etherpropoxyand so on

d. alkenyl side chains are named alphabetically in front

1. vinyl
2. allyl
e. stereochemical designations come in front as prefixes
1. alkenescis/trans/E/Z
2. alkanesR/S
7. Suffixes
a. alcohols are named by dropping e and adding ol
b. alkenes are named by changing ending to ene. the location
of the first carbon is placed in front of alkane name
1. butane to butene
propane to propene
if double bond is at 1 st carbon1-octene
if double bond is at 2 nd carbon2-octene
if double bond is at 3 rd carbon3-octene
c. if two double bondsdiene, three double bondstriene
1. 8 carbon unit with double bonds at 1 st and 5th would be
1,5-octadiene
2. 9 carbon unit with double bonds at 1 st, 4th and 7th
1,4,7-octatriene
d. alkynes use the same rules as alkenes but change ending to yne.
8. Cyclic Alkanes/Alkenes
a. use all previous rules add cyclo to root name(i.e octane
becomes cyclooctane; 2-hexene becomes 2-cyclohexene)
b. if a double bond is present it will be numbered 1 and 2.
Numbering will precede to get to the substituent with lowest
number.

1. if there is more than one substituent present use rules

for alkanes(I.E. 2,2,3 is better than 2,2,5. if two equal
substituents can be reached use alphabetical to
determine which direction to precede.
2. if an alcohol is present it will be the 1st carbon and then
precede to the next closest substituent in either
clockwise or anticlockwise manner.
9. Other alkyl/alkene rules
a. when there is a cyclic chain attached to an alkyl group, the
larger group becomes the base name.
1. cyclohexane ring with a pentyl group will be called
1-pentylcyclohexane
2. cyclopentyl ring with a hexane group will be called
1-cyclopentylhexane
b. if an alkyl substituent is complex, use nomenclature rules to
name it as its own molecule then change ending to yl.
1. 2,3-dimethy-4-propyloctane becomes 2,3-dimethyl4-propyloctyl
10. Bicyclics
a. the total number of carbons in the ring becomes the parent
name with the word bicyclo in front.
b. the carbons where the rings are fused are called bridgehead
carbons.
c. the carbons between the bridgeheads are called bridges
d. between bicyclo and the parent name is inserted in brackets
the number of carbons of each bridge in order of decreasing
length(bicyclo[3.2.1]octane). Periods are used to separate
the numbers.

3-methyloctane

4-methyldecane

5-propylundecane

2,8-dimethyldecane
Br

2-bromo-9-methyldecane

3,4,8-trimethyldecane

7,9-dimethyldec-4-ene
OH

dec-8-en-3-ol or 8-decen-3-ol

6-bromo-10-chloro-8-ethyl-4-methoxydecan-2-ol
Cl

Br

OH

OH

4-bromocyclohex-2-enol

Br

4-bromo-2-ethyl-1-methylcyclohexane

Br

2,5,7-trimethylcycloocta-1,3,5,7-tetraenol

OH
OH

2-methylbicyclo[2.2.1]heptan-7-ol
bicyclo[2.2.2]octane

2-methylbicyclo[2.2.1]hept-2-ene
bicyclo[3.3.2]decane

More information on bicyclics...

On bicyclics, the longest chain is always numbered 1st then the next longest...
In naming bicyclics, the name is bicyclo[x.y.z]alkane, for example. Number to
get to the substituent quickest in the longest chain. Substituents in shorter chains
DO NOT take precedence over any substituent in a longer chain.
11
10
6

4
5

7
1

9
8

11

10

Br

10

11

4
5

3
2

Br

11

7
1

10

Br

9
6

3
2

9
6

OH

11. Common names

a. alkyl halides are often named by a common name(pentyl
chloride instead of 1-chloropentane).
b. alcohols are often named by common name(ethyl alcohol
instead of 1-ethanol).
c. other common names include acetic acid, formic acid,
ethyl alcohol, ethylene glycol, glycerol, isopropyl alcohol,
acetylene, dichloromethane, chloroform
12. Hydrogens
a.
b.
c.
d.

Carbon with 3 Hsprimary hydrogens/carbon

Carbon with 2 Hssecondary hydrogens/carbon
Carbon with 1 Htertiary hydrogen/carbon
Carbon with 0 Hquarternary carbon

RULES FOR NOMENCLATURE

Select the longest chain and name it methane, ethane,.
If cyclic add prefix cyclo.
If contains double bond change ending from -ane to ene.
If there is an alcohol, number the chain to get to the alcohol first.
If there is no alcohol but there is a triple bond, number the chain to get to the triple bond first.
If there is no alcohol or a triple bond but there is a double bond, number the chain to get to the
double bond first.
If no alcohol or double or triple bonds, number the chain starting with the end with a
functional group.
If there is not a functional group on the first carbon go to the second
If there are functional groups on both sides, priority is determined by alphabet. I. E. A
bromine would get preference over a chlorine.
If there are substituents hanging off the base chain name them.
Iiodo, Brbromo, Clchloro, FFluoro
If there are more than one substituent you can group them together with prefixes.
2di, 3tri, 4tetra, 5penta, 6hexa
Put all substituents in alphabetical order with a number to indicate their position on the base
chain.
Separate numbers with commas. Separate numbers from letters with dashes.
If there are two substituents on the same carbon you must use the number twice.
The position of double and triple bonds are indicated by a number in front of the base name.
If there are more than one double or triple bond you use the prefixes as above, i.e.
di, tri, tetraFor example, hexane with two double bonds is 1,3-hexadiene.
Cyclic compound are numbered with largest group being number 1. The numbering then
proceeds in whichever direction gets to the next group quickest.

10

EXAMPLES
First, the molecule is 10 carbons in length so it is a decane. Since there are double bonds
it becomes decadiene. Since there are no alcohols, alkenes become highest priority. The
two methyls are combined into one name. Therefore, the name of this molecule is

6,8-dimethyl-1,3-decadiene
First, the molecule contains 6 carbons in a circle with a double bond. Thus, the base
name is cyclohexene. A double bond in a carbon will always be the first carbon. We
then head towards the bromine since bromine is alphabetically before methyl.
Br

3-bromo-6-methyl-1-cyclohexene
First the base chain is heptane. We could number it from either side and get to a group
at carbon #2. Since Br comes first alphabetically before Cl we number from the left to
right. Therefore,

Br

Cl

2-bromo-6-chloro-4,4-dimethylheptane
First the base chain is 9 carbons long with a double bond so it is nonene. If we number
from the right we start with chlorine. From the left we start with double bond. Since
double bonds take precedence over all non alcohol compounds we number from the left.
Cl

9-chloro-4,4,5,6,6,7-hexamethyl-1-nonene

11

OH

Alcohols always are numbered to be as low as possible. We would name this

compound 4-iodo-2-buten-1-ol.
Br

OH

OH

We would name this compound 2-bromo-3-fluoro-2,4-octadiene-1,5-diol

OH

Here the longest chain is 11 carbons long. See if you can find it. In either
direction alcohol comes on the 6 carbon. If you number from the left you get to
the double bond at the third carbon. From the right there is a methyl on the
second carbon. Therefore, this is 2-methyl-4,6,8-undecatrien-6-ol.

At first glance you may try to number this from the left. There is an ethyl on the
third carbon from the left and a methyl on the third carbon from the right. By
rule ethyl comes alphabetically before methyl so you would assume that you
would number from the left. But actually you number from the right because
double bonds have the highest priority.
7-ethyl-3-methyl-4-nonene is the correct name.

12

I. For the following structures give the name.

Br

Br

Cl

II. For the following names give the structure.

1. Octene
2. Cycloheptane
3. 4-methylnonane
4. 1,3-cyclooctadiene
5. 2-bromo-3-chlorobutane
6. 1-ethyl-2-methyl-3-pentylcyclopropane
7. 1,3,5-cyclohexatriene
8. 3-ethyl-4-fluoro-5,6,7-trimethyldecane
9. 3-bromo-1-cyclopentene
10. 7-methyl-5-propyl-3-octyne

13

I. For the following structures give the name.

4-ethyl-6-methylnonane
Br

3-bromo-heptene

6,7,8-trimethyl-3-decene

4-propylcyclohexene

3-bromo-5-ethyl-1,5-octadiene
Br

1,2,3-trimethylcyclopropane

4-methyl-1-pentyne
Cl

1-chlorocyclopentene

1,3,5,7-cyclooctatetraene

7-methyl-3,5-nonadiene

14

II. For the following names give the structure.

1. Octene

2. Cycloheptane

3. 4-methylnonane

4. 1,3-cyclooctadiene

5. 2-bromo-3-chlorobutane
Cl

Br

15

6. 1-ethyl-2-methyl-3-pentylcyclopropane
Technically, the name I gave is wrong. This
should be named based on pentyl side chain. It
should be called
1-(2-ethyl-3-methylcyclopropanyl)pentane

7. 1,3,5-cyclohexatriene

8. 3-ethyl-4-fluoro-5,6,7-trimethyldecane
F

9. 3-bromo-1-cyclopentene
Br

10. 7-methyl-5-propyl-3-octyne

16

Practice ProblemsChapter 4Nomenclature

OH

B
Br

Cl

Br

E
D

OH

OH

OH
F
Br

Cl
Br

OH

Br

Br

J
F

17

Draw the structures of the following:

1. 5-methyl-4-propyl-2,4,6,8,10-pentadecapenten-1-ol
2. Bicyclo[4.2.1]nonane
3. 3-chloro-4,5,6-trimethyl-1,4-cycloheptadien-1-ol
4. 5-sec-butyl-2-chloro-3-ethyl-8,9,9,11,12,13-hexamethyl-1,3,5-octadecatriene
5. 1-cyclopentyl-2-bromo-4-penten-2-ol
6. 1-bromo-2-chloro-3-ethyl-4-isobutyl-5- isopropyl-6- methyl-7-pentyl-1,3,5cycloheptatriene
7. 2-chloro-4,5-diethyl-7-iodo-3-vinyl-1,3-octadiene
8. 6-allyl-2-tert-butyl-3-chloro-5-ethyl-7,8,9-trimethyl-8-decen-6-ol
(after drawing this molecule rename it from the picture. You will come up with a
different name because the name above has a mistake. What is the mistake?)
9. 1-bromo-3-chloro-4-(2-cyclopropyl-3-ethyl -4,5-diiodo-4-octenyl)-2-nonene
(after drawing this molecule rename it from the picture. You will come up with a
different name because the name above has a mistake. What is the mistake?)
10. 2,3-dichloro-4,6-diethylbicyclo[4.3.2]undecane

18

Answer Key to Practice Problems

A. 4-allyl-7-bromo-6-chloro-2,8-cyclononadien-1-ol
B. 4-ethyl-3,7,8-trimethyl-5-decene
C. 4-bromo-8-fluorobicyclo[10.2.2]hexadecane
D. 5-ethyl-3,4,6,7-tetramethyl-2,4,6-nonatrien-1,9-diol
E. 5-ethyl-6-(1-fluorobutanyl)-4-isopropyl-3,8-tridecadien-2-ol
F. 8-bromo-5-sec-butyl-7-chloro-4-fluoro-6-methyl-2-nonene
G. 5-(2-bromo-6,6-dimethyl-2,4-cyclohexadien-3-olyl)-4,4,6,8,9,9,10,10octamethyl-1,5,7-undecatriene
H. 4-bromo-1-(3-ethyl-2,4-dimethylcyclobutanyl)-2-pentene
I. bicyclo[5.2.2]undecane
J. 2-bromo-8-butyl-11-tert-butyl-17-fluoro-6-isopropyl-3,4,16-trimethyl4,8,14-octadecatriene
1.

OH

2.

19

3.
OH

Cl

4.
Cl

5.
HO

Br

20

6.
Br
Cl

7.
Cl

8.

HO

Cl

The correct name is 5-allyl-8-chloro-6-ethyl-2,3,4,9,10,10-hexamethyl2-undecen-5-ol

21

9.

Br

Cl

The correct name is 9-(3-bromo-1-chloro-1-propenyl)-7-cyclopropyl-6-ethyl4,5-diiodo-4-tetradecene

10.
Cl
Cl

22

Br

Br

Br

Br

Cl

Cl

Cl

Br
OH

Br

OH

Br

23

3-bromohexane

Br

Br
2

2-bromo-5-methylheptane

Br

Cl

Br

Cl

Cl

3-bromo-7-chlorononane

2,7-dibromo-3,5-dichlorooctane

Br
OH
2

7-bromooctan-4-ol

Br

Br

OH

2
1

4
3

6
5

9-bromo-7-methylnon-2-en-5-ol

8
7

9-bromo-7-methyl-2-nonen-5-ol

10
9

Br

9-bromodec-4-ene

9-bromo-4-decene

24

4. Physical Properties
mp/bp
C 1-4gases; 5-17liquids; 18+--solids
as molecular weight increasebp/mp increases
as branching increasesbp decreases
symmetry increases mp
Density
very low; halogens increase density considerably
Solubility(alkanes)
very low in water
high solubility in low polar solvents
5. Conformational analysis
a. Newman projections
1. eclipsed/staggered/anti/gauche
anti staggered most favorable
eclipsed least favorable
gauche in between eclipsed and staggered
gauche is the non favored staggered positions
anti is the most favored staggered positions
eclipsed have favored and non favored positions also

25

Draw the Newman conformation for the following molecule exactly as drawn sighting down
the indicated carbons. Then draw the other 5 conformations in order by rotating the front
carbon clockwise.

sight down Carbons

2-3 with 2 in
Cl
front

tert-butyl is largest group, then phenyl,

then pentyl chain, then Cl, then H.

26

Draw the Newman conformation for the following molecule exactly as drawn sighting down
the indicated carbons. Then draw the other 5 conformations in order by rotating the front
carbon clockwise.

sight down Carbons

2-3 with 2 in
Cl
front

C H3
H

Ph

Cl

C 4H 9
C 5H 12

C 4 H9
H

Ph

tert-butyl is largest group, then phenyl,

then pentyl chain, then Cl, then H.

Cl
H

Ph
C H3

C4 H9 C H
5 12

Ph

Cl
H3 C C 5 H1 2

H3 C

P
h

C 4H 9

C
H

C 5 H 123

C4 H 9
H

Cl

H 3C
H

P
h
C
4

Cl
C 5 H 12

Cl

H
C5 H1 2

27

Draw the Newman projections for the following molecule. In the first picture draw the
molecule exactly as shown. Holding the first carbon fixed, rotate the back carbon to
show all 6 conformations of this picture. Identify the gauche, anti and eclipsed pictures.
Ph

OH

Size Ph > Hexyl > F and CH3 > OH > H

Ph

CH3
Ph

OH
Hexyl

OH

Size Ph > hexyl > F and CH3 > OH > H

Hexyl
F
OH

H
Hexyl

GAUCHE
Hexyl CH3

CH3

Ph CH 3

ECLIPSED

ECLIPSED

OH
F

GAUCHE
F CH3

CH 3
Ph
OH

Ph

Hexyl

OH
Ph

ANTI

H
Ph

He
xyl
OH

ECLIPSED

28

6. Cyclic Alkanes/Ring Strain

a. ring strain
1. heats of combustion have been used to determine ring strain
2. table 4.6 page 155
cyclopropane has greatest ring strain. cyclononane,
cyclodecane and cyclooctane come next in ring strain.
cyclopentane and heptane have very little ring strain
cyclopentadecane and cyclohexane have almost no ring strain
3. angle strain makes up most of ring strain
due to angles being less than the tetrahedral angles that
are preferred
cyclopropane is 60 degrees instead of 109.5
because of ring strain orbital overlap is low which
weakens bonds.
4. Torsional strain due to locked ring structures leads to eclipsed
newman projections
cyclobutane actually is not planar(like a square) but bent.
in bent conformation angles are 88 degrees which is even
further from 109.5 than the 90 degrees of a square. However,
the bent structure provides much less torsional strain which
makes it a more favorable structure than the planar form.
cyclopentane has angle of 108 vs 109.5 if planar. Therefore
little angle strain. However it doesnt take this form due to
intense torsional strain. Almost all of the ring strain is due to
torsional strain. Therefore it bends out of plane increasing
its angle strain but relieving its torsional strain
cyclohexane has a form that has almost no angle or torsional
strain.

29

7. Cyclohexane
a. boat vs. chair
1. cyclohexane actually has 7 conformations it can take.
However, the boat and chair forms predominate. The chair
form is free of ring and torsional strain. The boat form is
free of ring strain but has torsional strain. Based on thermodynamical data, 99% of cyclohexane molecules exist in the
chair form.
2. Boat has torsional strain(due to eclipsed hydrogens2 and 3
eclipsed, 5 and 6 eclipsed).
Boat has flagpole interactions(due to van der Waal
interactions between H-1 and H-4).
3. half-twist forms has less torsional strain and less flagpole
interactions
4. cycloheptane, cyclooctane, cyclodecanehave small to no
ring strain. Most strain is due to eclipsed
hydrogens(torsional strain) and due to van der waal
interactions also called transannular strain.
b. axial vs equatorial
1. there are 6 equatorial and 6 axial positions on chair form
2. the equatorial positions are best for larger group as
the equatorial positions avoid van der waal interactions.
3. As cyclohexane flips through all the axial positions become
equatorial and vice versa
4. In cyclohexane these interactions are called 1,3 diaxial
interactions. They are akin to gauche interactions in
butane newman conformations.
5. as stated in #2, larger groups prefer equatorial position
because larger groups will have larger diaxial interactions.

30

c. cis vs trans in disubstituted alkanes

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12,

1,2 cis are e,a and a,e

1,2 trans are e,e and a,a
1,3 cis are e,e and a,a
1,3 trans are e,a and a,e
1,4 cis are e,a and a,e
1,4 trans are e,e and a,a
1,2 cis is meso; 1,2 trans is pair of enantiomers
1,3 cis is meso; 1,3 trans is pair of enantionmers
1,4 cis is meso and 1,4 trans is meso.
1,4 cis is a diastereomer of 1,4 trans
1,3 cis is a diastereomer of 1,3 trans
1,2 cis is a diastereomer of 1,2 trans

8. Decalin/other bicyclics
a. Know structures for decalin(cis and trans)
b. Know adamantine, diamond, cubane, prismane, and
bicyclo[1.1.0]butane, dodecahedrane
9. Pheremones
a. undecane, 2-methylheptadecane, muscalure
10. Synthesis/Retrosynthesis
a. hydrogenation of alkenes/alkynes
b. reduction of alkyl halides
c. deprotonation of alkynes/alkylation of alkynide ions
d. retrosynthesis/identity of precursors/E. J. Corey

31

RING FLIP OF CHAIR

CHAIR
A

B
A

B
B

B
B

A
B

3
2

A
B

A
B

CIS 1,2 and ring flip

5

5
3

CIS 1,3 and ring flip

5

5
3

CIS 1,4 and ring flip

3
2

5
4

2
3

32

CHAIR

RING FLIP OF CHAIR

B
A

B
5

B
B

A
B

3
2

A
A

B
B

TRANS 1,2 and ring flip

A

5
2

A
A

TRANS 1,3 and ring flip

A

5
2

B
B

TRANS 1,4 and ring flip

A

6
3
2

A
4

5
1

2
3

33

Draw the following cyclohexane in chair form. Draw the other chair form by
flipping the chair. Pick which one is the more favored product.
Phenyl > tert-butyl > pentyl > OH

OH

up
4

up

d ow n
2

5
6

up
OH

OH
4

3
5

Ph
1

OH

be tte r pi cture all grou ps equ ato rial

2
6

34

Homework #2Give the name for the structures below.

OH

Br

Br
F
OH

OH

Br

35

Redraw the following molecule in Newman Configuration in the first box. Put carbon 4 in front
and carbon 5 behind. Then draw the other 5 main Newman Configurations by rotating the
BACK carbon counterclockwise. Label the configurations, gauche, anti, eclipsed
Cl
1

3
2

5
4

Br

Ph
7
6

9
8

10

On carbon 4--Br is largest, next is propyl, and

hydrogen is the smallest.
On carbon 5--phenyl is largest, next is pentyl,
and hydrogen is the smallest.

36

Draw the following two molecules in chair configuration, then draw the ring flip of each.

Br

Cl

37

Homework #2Give the name for the structures below.

OH

Br

11-bromo-6-ethyl-13-fluoro-9-methyl-8-vinyl-2,6-tridecadien-5-ol

Br
F

7-bromo-2-fluorobicyclo[4.2.2]decane

OH

7,10-dimethylbicyclo[4.4.0]decan-3-ol

OH

Br

8-(3-bromo-2-methyl-2-pentenyl)-11-ethyl-10-isobutyl-4-isopropyl-3,7,11,13tetradecatetraen-7-ol

38

Redraw the following molecule in Newman Configuration in the first box. Put carbon 4 in front
and carbon 5 behind. Then draw the other 5 main Newman Configurations by rotating the
BACK carbon counterclockwise. Label the configurations, gauche, anti, eclipsed
Cl
1

Ph
5

Br

7
6

On carbon 4--Br is largest, next is propyl, and

hydrogen is the smallest.
On carbon 5--phenyl is largest, next is pentyl,
and hydrogen is the smallest.

9
8

10

ANTI

ECLIPSED

P Ph

Cl

Ph

Br

Cl
Br

GAUCHE

P Pentyl

H
Cl

Ph

Pentyl

Br

H
Cl

ECLIPSED
P Cl

P
Pentyl

Ph
Br

H
Pentyl

Pentyl

ECLIPSED

GAUCHE

Cl

Br

H
PH

Pentyl
Br

Ph

39

Draw the following two molecules in chair configuration, then draw the ring flip of each.

4
5

Br
6

Br

5
1

4
1

Br

4
3

6
1

Cl

5
1

Cl

4
2

3
3
5

4
1

Cl

40

Pe
OH
tBu

1
2

5
4

Ph
6

2
4

HO

3
OH

Ph
Pe

OH

HO

3
6

tBu

41

Br
CH3

H3C

Cl

4
5
3

6
4

1
OH

OH
Cl

1
6

3
4
Br

6
3

Br

H3C

1
2

OH
Cl

42

HO
Cl

1
6
2

5
3

Br

Br

H3C

Cl
6

4
5

1
CH3
Cl up OH
CH3 down

HO
1

4
Br

43

44

IndexofHydrogenDeficiency

InordertocalculatetheIndexofHydrogenDeficiency(I.H.D.),youneedtoknowthefollowing:

1)FormulaofsaturatedalkaneisCnH2n+2.

2)Eachhalogenisreplacedbyaddingonehydrogen.

3)Eachoxygenisreplacedbyaddingzerohydrogen.

4)Eachnitrogenisreplacedbysubtractingonehydrogen.

5)AfterconvertingformulatoCxHy,countthemissinghydrogenfromthe
saturatedalkaneandthendividethatbytwotogettheI.H.D.

EXAMPLES

C10H20

First,converttoCxHy(alreadydone),C10H20

2ndfigureoutthesaturatedalkane;CnH2n+2,n=10,soC10H2(10)+2orC10H22

3rdfigureouthowmanyHaremissing;2220=2

4th,dividethenumberofmissingHby2;2/2=1I.H.D

C15H26

First,converttoCxHy(alreadydone),C15H26

2ndfigureoutthesaturatedalkane;CnH2n+2,n=15,soC15H2(15)+2orC10H32

3rdfigureouthowmanyHaremissing;3226=6

4th,dividethenumberofmissingHby2;6/2=3I.H.D

C12H20Br2

First,converttoCxHy(eachhalogen=1H),C12H20Br2=C12H20H2=C12H22

2ndfigureoutthesaturatedalkane;CnH2n+2,n=12,soC12H2(12)+2orC10H26

3rdfigureouthowmanyHaremissing;2622=4

4th,dividethenumberofmissingHby2;4/2=2I.H.D

45
C10H18ClF

First,converttoCxHy(eachhalogen=1H),C10H18ClF=C10H18HH=C10H20

2ndfigureoutthesaturatedalkane;CnH2n+2,n=10,soC10H2(10)+2orC10H22

3rdfigureouthowmanyHaremissing;2220=2

4th,dividethenumberofmissingHby2;2/2=1I.H.D

C15H24Br2O2

First,converttoCxHy(eachhalogen=1H,oxygen=0H),C15H24Br2O2=C15H24H2=C15H26

2ndfigureoutthesaturatedalkane;CnH2n+2,n=15,soC15H2(15)+2orC15H32

3rdfigureouthowmanyHaremissing;3226=6

4th,dividethenumberofmissingHby2;6/2=3I.H.D

C18H26O2N2

First,converttoCxHy(Halogen=1H,O=0H,N=1H),C18H26O2N2=C18H26H2=C18H24

2ndfigureoutthesaturatedalkane;CnH2n+2,n=18,soC18H2(18)+2orC18H38

3rdfigureouthowmanyHaremissing;3824=14

4th,dividethenumberofmissingHby2;14/2=7I.H.D

C20H35Br3N2O

First,converttoCxHy(Halogen=1H,O=0H,N=1H),C20H35Br3N2O=C20H35H3H2=C20H36

2ndfigureoutthesaturatedalkane;CnH2n+2,n=20,soC20H2(20)+2orC20H42

3rdfigureouthowmanyHaremissing;4236=6

4th,dividethenumberofmissingHby2;6/2=3I.H.D

C24H40Cl2F2O3N2

First,converttoCxHy(Halogen=1H,O=0H,N=1H),C24H40Cl2F2O3N2=C24H40H4H2=C24H42

2ndfigureoutthesaturatedalkane;CnH2n+2,n=24,soC24H2(24)+2orC24H50

3rdfigureouthowmanyHaremissing;5042=8
4th,dividethenumberofmissingHby2;8/2=4I.H.D

46

Homework #2

Name:

Draw the Newman conformation for the following molecule exactly as drawn sighting
down the indicated carbons. Then draw the other 5 conformations in order by rotating
the front carbon clockwise. Label the anti, the 2 gauche and the 3 eclipsed. Circle the
most energetically unfavorable drawing amongst the 6.
Size of groups on the front carbon:
Size of groups on the front carbon:

Br

HO

t-Bu

Bromine
t-butyl

>
>

Methyl > Hydrogen

Pentyl > Hydroxy (OH)

47

Name the following

Br

OH

48

Draw the following.

2-isopropyl-3,4,5-trimethyloctene

2,4-dibromocyclohept-2-4-dien-1-ol

2-bromobicyclo[4.2.2]decane

Draw this product in the chair configuration. Draw the ring flip of what you just drew
and then pick the best picture.
t-Bu
Cl

OH
Oh

49

Homework #2KEY
Draw the Newman conformation for the following molecule exactly as drawn sighting
down the indicated carbons. Then draw the other 5 conformations in order by rotating
the front carbon clockwise. Label the anti, the 2 gauche and the 3 eclipsed. Circle the
most energetically unfavorable drawing amongst the 6.
Size of groups on the front carbon:
Size of groups on the front carbon:

Bromine
t-butyl

Methyl > Hydrogen

Pentyl > Hydroxy (OH)

Br

HO

t-Bu

Pe H

Pe
H

Pe

Br

HO

tBu
Me

GAUCHE

Pe Me
Br
HO

>
>

tBu
H

ECLIPSED

Me
HO

tBu
Br

Me

HO

tBu
Br

WORST ECLIPSED

GAUCHE

Pe

Pe Br

Br

Me

HO

tBu
H

ANTI

H
HO

tBu
Me

ECLIPSED

50

Name the following

3,4,6-trimethyloctane

4,8-dimethylnona-2,5-diene

Br

6-bromo-1-methylcyclohex-1-ene

4,5-dimethylcycloocta-2,4-dienol

OH

51

Draw the following.

1
2

8
7

2-isopropyl-3,4,5-trimethyloctene

OH
1

5
2
4

Br

Br

2,4-dibromocyclohept-2-4-dien-1-ol
5

8
2

Br

Draw this product in the chair configuration. Draw the ring flip of what you just drew
and then pick the best picture.
t-Bu
Br
Cl
Cl
HO
OH
OH

Cl

t-Bu

OH
OH
t-Bu

52

Homework #2

Name:

Draw the Newman conformation for the following molecule exactly as drawn sighting
down the indicated carbons. Then draw the other 5 conformations in order by rotating
the front carbon clockwise. Label the anti, the 2 gauche and the 3 eclipsed. Circle the
most energetically unfavorable drawing amongst the 6.
Size of groups on the front carbon:
Size of groups on the front carbon:

HO

Phenyl
>
Isopropyl >

Propyl > Hydrogen

Butyl > Hydroxy (OH)

53

Name the following

OH

Br

O
Cl

OCH3

54

Draw the following.

2-bromo-4-methylhept-1,3-diene

4-chloro-3-isopropyl-2-methylcyclohexanol

3-methylbicyclo[4.2.1]noneane

Draw this product in the chair configuration. Draw the ring flip of what you just drew
and then pick the best picture.
OH
CH3

Ph
Br

55

Homework #2KEY
Draw the Newman conformation for the following molecule exactly as drawn sighting
down the indicated carbons. Then draw the other 5 conformations in order by rotating
the front carbon clockwise. Label the anti, the 2 gauche and the 3 eclipsed. Circle the
most energetically unfavorable drawing amongst the 6.
Size of groups on the front carbon:
Size of groups on the front carbon:

Phenyl
>
Isopropyl >

Propyl > Hydrogen

Butyl > Hydroxy (OH)

HO

Bu H

Bu
H

Ph

HO

iPr
Pr

GAUCHE

Bu Pr
Ph
HO

iPr

ECLIPSED

Pr
HO

Ph

Bu

iPr

Pr

HO

IPr
Ph

WORST ECLIPSED

GAUCHE

Bu Ph

Bu
Ph

Pr

HO

IPr
H

ANTI

H
HO

Pr

iPr

ECLIPSED

56

Name the following

2,3,4,6-tetramethylheptane

OH

5-isopropyl-8-methylnona-6,8-dien-2-ol

Br

2-bromo-3-chloro-6-ethoxy-3-methylheptane

Cl

3-methoxy-1,6-dimethylcyclohex-1-ene

OCH3

57

Draw the following.

Br
2

2-bromo-4-methylhept-1,3-diene

Cl

3
2

HO

4-chloro-3-isopropyl-2-methylcyclohexanol

2
1

8
9
7

4
6

3-methylbicyclo[4.2.1]nonane

Draw this product in the chair configuration. Draw the ring flip of what you just drew
and then pick the best picture.
OH

Br

OH
CH3

CH3
CH3
Br

Ph
Br

OH
Ph
Ph