Department of Chemistry & Biochemistry

Chemistry 221 2016 Fall Introductory Organic Chemistry I

Textbook: Introductory Organic Chemistry Course Pack (CHEM 221)

Instructor: Louis Cuccia

Office: L-SP 275-17
Office hours: Thursday: 3:00 - 5:00
Email: cuccial@alcor.concordia.ca (CHEM221 as the subject)
Course web site: Moodle
Strategic Learning leader: Mona Hashemi
Strategic Learning Sessions (starting September 12, 2016):
Mondays 2:45-4:00 pm; room CC-308
Thursdays 4:15-5:30 pm; room CC-320
1

Organic Chemistry Chemistry of Life and Beyond..

Synthesis

Functional Groups

Reactions

nomenclature

Mechanisms
electron
movement

Molecules
formula
shape
name
bonding

Old coursepack 3-14 & 43-90

Atoms

New coursepack 3-8 & 23-46

Free chemical drawing program Accelrys Draw:
http://accelrys.com/resource-center/downloads/freeware/index.html

Hybrid Orbitals
Hybridization of orbitals (L. Pauling).
the combination of two or more atomic orbitals forms a new
set of atomic orbitals, called hybrid orbitals.
We deal with three types of hybrid orbitals.
sp3 (one s orbital + three p orbitals).
sp2 (one s orbital + two p orbitals).
sp (one s orbital + one p orbital).
Overlap of hybrid orbitals can form two types of bonds.
depending on the geometry of overlap.
bonds are formed by direct overlap.
bonds are formed by parallel overlap.
3

2
sp

Hybrid Orbitals

One pure s orbital

Two pure p orbitals

+

Three hybrid sp2 atomic

orbitals
4

3 hybrid

The three sp2 orbitals

each contain 1 electron
and orient themselves as
far apart from each other
as possible - along the
corners of a triangle
(trigonal planar).

2
sp

orbitals

Consider ethylene, C2H4:

The Lewis structure is:

2pz

(C2pz, C2pz)
sp2

2pz

sp2

sp2

sp2

sp2

sp2

(Csp2, H1s)
(Csp2, Csp2)

2p
2s
1s
ground state of C

2pz

hybridize
s + px + py

sp2
1s
sp2 hybridized carbon

2pz Orbitals and the Bond

One p orbital on each C of ethene forms a
bond
Overlapping sp2 orbitals forms a bond.
The bond is perpendicular to the bond.

Bonding in ethylene
Three sp2 orbitals and an
unhybridized 2p orbital

Double bond 1 bond (orbital overlab between nuclei) + 1

bond (orbital overlap above and below the s bond).

There is less favourable overlap in bonding compared to

bonding.
Therefore bonding is weaker than bonding.
A single bond between two atoms is always a bond.
A double bond is a combination of a bond and a bond.

The C=C double bond is made up of 1 bond and 1 bond.

It is stronger than a C-C single bond and more difficult to break.
H

H
C
H

H
H

Rotation around the C=C bond causes the p orbitals to

become perpendicular and thus to lose their overlap.
The bond would thus be broken and would cost about
70 kcal/mol.
This is a large energy barrier, and rotation around the
C=C double bond does not occur at room temperature.
10

STANDARD SYMBOLS
Types of bonds: and
n

H3C

CH3

non-bonded pairs: n
11

sp Hybrid Orbitals
s

+ p

= 2 sp

x
Two lobes of unequal
size at an angle of
180 .
y
Two sp orbitals on the
y axis (only showing
the major lobes) 180
12

Consider ethyne, C2H2:

The Lewis structure is:

H
C
C
H

2p
2s
1s
ground state of C
13

Consider ethyne, C2H2:

The Lewis structure is:

H
C
C
H

The carbons are sp hybridized.

they each have two sp hybrid orbitals 180
perpendicular p orbitals.

apart, as well as two

The C sp orbitals will form bonds to each other and to the H 1s

orbitals.
The two p orbitals will form two mutually perpendicular bonds.
2p
2s
1s
ground state of C

2p

hybridize
s + pz

sp
1s
sp hybridized carbon

14

sp Hybrid Orbitals

an sp orbital

two sp orbitals

Two sp orbitals and two unhybridized 2p orbitals (note that one of the 2py lobes
should be blue).
The two unhybridized 2p orbitals are perpendicular to each other and to the two
sp hybrid orbitals.
15

Acetylene

16

Triple Bond
1 bond

2 bonds
The CC triple bond is made up of one bond and two bonds.
The bond energies (strenghts) are: E(CC) > E(C=C) > E(C-C)
17

Hybridization rules:
To describe bonding in a molecule:
1. Draw the Lewis structure of the molecule.
2. Find the coordination number of the atom (= number of atoms bonded
to the atom + number of lone pairs) This is the same as the coordination
number of VSEPR.
3. If CN = 4, hybridization is sp3, the atom has four sp3 hybrid orbitals in a
tetrahedral geometry with 109.5 angles.
If CN = 3, hybridization is sp2, the atom has three sp2 hybrid orbitals in a
trigonal planar geometry with 120 angles. There is also a p orbital
perpendicular to the plane of the sp2 orbitals.
If CN = 2, hybridization is sp, the atom has two sp hybrid orbitals in a
linear geometry with 180 angles. There are also two p orbital
perpendicular to the plane of the sp orbitals.
18

sp3

(CH2)nCH3

sp3

NH2 amines

sp3

OH alcohols

sp3

sp2

R ethers

CN

aldehydes
H

OH

O
2
s
p

nitrile

carboxylic

C
R

ketones

alkyn

s
p

2
s
p

sp2

CC

alkenes

sp2

s
p

esters

C
R

OR
19

Summary
Single bonds:

Always

Double bonds:

1+1

Triple bonds:

1+2

If the coordination number = 2, the hybridization is sp

If the coordination number = 3, the hybridization is sp2
If the coordination number = 4, the hybridization is sp3
(remember to include lone pairs of electrons)

20

Covalent bond length in relation to bond hybridization

Carbon atoms are held closer together by multiple bonds than
by single bonds.
triple bond length < double bond length < single bond length
Because s orbitals are closer to the nucleus than are p
orbitals, hybrid orbitals with greater s character are shorter
and more electronegative.
Csp3-Csp3 single bond 1.53 25%s & 25%s
Csp3-Csp2 single bond 1.50 25%s & 33%s
Csp3-Csp single bond 1.46 25%s & 50%s
shorter bonds are also stronger bonds.
CC strength > C=C strength > C-C strength
21

BOND STRENGTHS - MULTIPLE BONDS

CC
bond

bond
type

bond
length

bond energy
per mole
Kcal

molecule
measured

(KJ)

C-C

sp3-sp3

1.54 A

83

(347)

CH3CH3

C=C

sp2-sp2

1.34 A

146

(611)

CH2=CH2

CC

sp - sp

1.20 A

(837)

HCCH

200

22

BOND STRENGTHS - MULTIPLE BONDS

CC
bond

bond
type

bond
length

bond energy
per mole
Kcal

(KJ)

molecule
measured

C-C

sp3-sp3

1.54 A

83

(347)

CH3CH3

C=C

sp2-sp2

1.34 A

146

(611)

CH2=CH2

CC

sp - sp

1.20 A

(837)

HCCH

increasing
s-character

shorter

200
stronger

Typical pi bonds have a bond

energy of about 50-60 kcal/mole

23

Orbitals and stability (C6H12)

H
H
C CH
C
H
C
CH
H
C
CH
H
C
C
3
3 H
3
2
3
2
3
2
3
C
C

C
C

C
C H
H
C
CH
2
2

H
C CH
CH
H
C
CH
C
3
3 H
3
3
2 H C
H H

sp2-sp2
sp2-sp3
sp3-sp3
Most stable

least stable

Bonds with more s character are more stable (lower energy

orbital).
sp2-sp3 bonds have more s character than sp3-sp3 bonds
The more substituted (with carbon) the alkene is the more stable.
24

Organic Chemistry Chemistry of Life and Beyond..

Synthesis

Functional Groups

Reactions

Mechanisms
electron
movement

Molecules
T.A.: Rachem Hall
Office Hours: Wed. 10:30-11:30
Office: SP 201.08
Email: rachel.y.hall@gmail.com

T.A.: Laura Rodriguez Solano

Office Hours: Mon. 1:15-2:15
Office: SP 265.30
Email: lanrosol@gmail.com

formula
shape
name
bonding

Atoms
25

Conformation
Conformation: any three-dimensional
arrangement of atoms in a molecule that
results from rotation about a single bond.
Newman projection: a way to view a
molecule by looking along a carboncarbon bond.

26

conformations of ethane

eclipsed conformation

The conformations of a molecule are different arrangements in space

of the atoms within the molecule due to rotation around single bonds.
The eclipsed conformation has all the carbon-hydrogen bonds lined
up. This is the maximum energy conformation.

27

conformations of ethane

staggered conformation

The staggered conformation has the bonding electrons of the carbonhydrogen bonds as far apart as possible.
This is the lowest energy conformation.
28

The relative positions of the hydrogen atoms on

the two carbon atoms are best represented with
a Newman Projection.

29

H
C
H H

C
H

A Newman projection is a view of a molecule down the axis of a

carbon-carbon bond. The carbon in the front is represented by a dot,
and the carbon in the back is represented by a circle.
30

H
C
H H

C
H

A Newman projection is a view of a molecule down the axis of a

carbon-carbon bond. The carbon in the front is represented by a
dot, and the carbon in the back is represented by a circle.
31

32

H
C
H H

C
H

A Newman projection is a view of a molecule down the axis of a

carbon-carbon bond. The carbon in the front is represented by a dot,
and the carbon in the back is represented by a circle.
33

H
C
H H

C
H

A Newman projection is a view of a molecule down the axis of a

carbon-carbon bond. The carbon in the front is represented by a
dot, and the carbon in the back is represented by a circle.
34

Staggered conformation
35

60

dihedral angle

H
H

staggered conformation

HH

HH

dihedral angle

H
H

eclipsed conformation

A Newman projection allows the visualization of the spacial

relationship between atoms bonded on adjacent carbon atoms.
The dihedral angle () is the angle between groups on adjacent
carbon atoms as viewed in the Newman projection formula.
36

60

dihedral angle

H
H

HH

HH

dihedral angle

H
H

37

 Staggered conformation: a conformation of a

carbon-carbon single bond where the atoms
on one carbon are as far apart as possible
from the atoms on the adjacent carbon.

38

 Eclipsed conformation: a conformation of a

carbon-carbon single bond where the atoms
on one carbon are as close as possible to the
atoms on the adjacent carbon.

39

Energetics for ethane

The difference in energy between the staggered and
eclipsed conformation of ethane is about 3 kcal/mol.

40

Energetics for ethane

Torsional strain: the force that opposes the rotation
of one part of a molecule about a bond while the
other part of the molecule is held fixed.
the torsional strain between eclipsed and staggered
ethane is approximately 3.4 kcal/mol.

3.4 kcal/mol

41

Energetics for ethane

42

eclipsed

43

eclipsed

Ball-and-stick

Space-filling

A 60 rotation converts the eclipsed conformation into the

staggered conformation

44

staggered

45

staggered

Ball-and-stick

Space-filling

46

 At room temperature, molecules have enough

kinetic energy to get over barriers as high as
20 kcal/mol.
Therefore at room temperature, rotation
around the C-C bond in ethane is constant.

But the molecules spend most of their time in

the more favorable staggered conformations.
47

consider butane
CH3CH2CH2CH3

CH3
H

H
CH3

HH

HH
C
H

C
HH

H
C
HH

The most stable conformation has a

dihedral angle of 180 between
the methyl groups.
This staggered conformation is
called the anti-conformation
48

consider butane
CH3CH2CH2CH3

HH

HH
C
H

C
HH

H
C
HH

CH3
H

H
CH3
49

Butane, CH3CH2CH2CH3
CH3
CH3
CH3 H3C
H

H
H

H
H

There are two other staggered conformations possible

for butane where there is a dihedral angle of 60
between the methyl groups.
These are called gauche conformations.
butane gauche conformation nonbonded interaction
strain is approx. 0.8 kcal/mol.
50

There are two different eclipsed

conformations for butane

methyl eclipsed with methyl

methyl eclipsed with hydrogen

51

Forces involved in conformational preferences

Weak attraction/repulsion that exists between nonpolar molecules
are known as van der Waals interactions.
These forces are the result of the motion of electrons within bonds
and molecules.
The motion of electrons creates small distortions in charge
distribution resulting in temporary induced dipoles.
The effective size of molecules are represented in terms of van der
Waals radii for each atom. (molecules are not balls and sticks, but
rather space-filling).
When molecules (or parts of the same molecule) are not too close,
attractive van der Waals interactions can occur.
However, if the distance is too short (less than the van der Waals
radii of the interacting atoms, repulsive (unfavourable) van der
Waals interactions occur.
52

Butane

Eclipsed

Eclipsed

53

Butane conformations
energy diagram

54

Butane conformations
energy diagram

eclipsed form

55

Butane conformations
energy diagram

gauche form

56

Butane conformations
energy diagram
5 kcal/mol

fully eclipsed form

57

Butane conformations

gauche form

58

Butane conformations
At room temperature, molecules have enough kinetic
energy to get over barriers as high as 20 kcal/mol.
Therefore at room temperature, there is rapid
interconversion between conformations in butane.
At room temperature, about 25% of butane molecules
are in gauche conformations, and 75% in the anti
conformation.

59

Energetics for butane

[anti]/[gauche] = 4

60

Which Newman projection represents that of butane, viewed along the C2-C3
bond with a dihedral angle of 60?

A)

C)

CH3

CH3
H

CH3

H
CH3

B) H3C
H

CH3
H
H H

D)

H
H

CH3

H
CH3

Hydrocarbons
space-filling models
Alkanes have the general formula CnH2n+2

10

Compounds that differ from each other in their molecular formulas

by the unit -CH2- are members of a homologous series.
62

All alkanes have similar chemical properties, but their

physical properties vary with molecular weight and and the
shape of the molecule
The boiling points of linear alkanes increase steadily with
molecular weight.
The weak forces of attraction that exist between non-polar
molecules are called van der Waals attractive interactions.
These forces are the result of the constant motion of
electrons within the bonds and molecules.
These motions can create small momentary dipoles that can
subsequently induce a momentary dipole of the opposite
direction in a neighboring molecule (induced dipole).
The favorable interaction of induced dipoles causes a slight
attraction between molecules.

63

As the alkane length increases, the amount of intermolecular interactions

between molecules can increase - more favorable van der Waals interactions.
64

Constitutional isomers differ in the the order and the

way in which the atoms are bonded together.
For example: C5H12
branched-chain

straight-chain

H3C

CH2

CH2

CH2

CH3

H3C

CH2
C

H CH3

n-pentane
bp 36.1 C
mp -129.7 C

CH3

CH3

2-methylbutane
bp 27.9 C
mp -159.9 C

C
H3C

CH3
CH3

2,2-dimethylpropane
bp 9.5 C
mp -16.6 C

n-alkanes - n stands for normal (i.e. linear)

Q. How can you account for the differences in boiling points?
A. Van der Waals interactions
65

Van der Waals interactions

66

Constitutional Isomerism
Mo le cular
F ormula
CH 4

Constit ut ional
Is omers

C 5 H1 2

1
3

C 1 0 H2 2

75

C 1 5 H3 2

4 ,3 4 7

C 2 5 H5 2

3 6,7 97,5 8 8

C 3 0 H6 2

4 ,1 1 1,84 6 ,7 6 3
67

Nomenclature - IUPAC

Suffix -ane specifies an alkane

Prefix tells the number of carbon atoms
Pr ef ix C arb ons
met h1
et h2
pr op 3
bu t4
pen t5
hex6
7
hep toct8
no n9
dec10

C arb ons
Pr ef ix
un dec11
do dec12
tr id ec13
tetr ad ec14
pen tad ec- 15
hexa dec16
hep tad ec- 17
octadec18
no nadec19
ei cos20
68

methane, CH4

CH 4

H C H
H

condensed
formula

Lewis
structure

HH
3D representation

space-filling
representation

All hydrogen atoms on the carbon are equivalent.

The clouds on the space filling representation is known as the van
der Waals radii.
If goups are too crowded in a molecule, unfavorable nonbonding
interactions known as van der Waals repulsions occur.
69

ethane, C2H6
CH 3CH 3
condensed
formula

This image
cannot currently
be displayed.

This image cannot

currently be
displayed.

Lewis
structure

3D representation

space-filling
representation

All hydrogen atoms in ethane are equivalent

This image
cannot
currently
be

chloroethane

This image
cannot
currently
be

chloroethane

This image
cannot
currently
be

chloroethane

This image
cannot
currently be
displayed.

chloroethane

Different representations of chloroethane - all four structural formulas

represent the SAME molecule. They all have the same connectivity.

70

There are two DIFFERENT ways to replace two hydrogen

atoms with two chlorine atoms:
Cl

C C
HH

HCl

1,1-dichloroethane

Cl

Cl

C C
HH

HH

1,2-dichloroethane

These compounds are constitutional isomers - the same

molecular formula, but different connectivities.
They have different physical properties (m.p., b.p.,
dipole moment.)
71

Propane, C3H8

CH 3CH 2CH 3

H C C C H
H H H

condensed
formula

H H H

Lewis
structure

C H
H C
C
H
H
HH
3D representation

space-filling
representation

H H H
H C C C H
H H H
two primary carbons and one secondary carbon.

72

Classification of C and H
Primary (1 ) C: a carbon bonded to one other carbon.
1 H: a hydrogen bonded to a 1 carbon.
Secondary (2 ) C: a carbon bonded to two other carbons.
2 H: a hydrogen bonded to a 2 carbon.
Tertiary (3 ) C: a carbon bonded to three other carbons.
3 H: a hydrogen bonded to a 3 carbon.
Quaternary (4 ) C: a carbon bonded to four other carbons.

73

Same classification for amines

Primary (1 ) amine: nitrogen bonded to one carbon.

R-NH2 e.g. CH3NH2 methylamine

Secondary (2 ) amine: nitrogen bonded to two carbons.

R2NH e.g. (CH3)2NH dimethylamine

Tertiary (3 ) amine: nitrogen bonded to three carbons.

R3N e.g. (CH3)3N trimethylamine

Quaternary (4 ) ammonium ion: nitrogen bonded to four carbons.

R4N+ e.g. (CH3)4N+Cl- tetramethylammonium chloride

74

Butane, C4H10

CH 3CH 2CH 2CH 3

condensed
formula

This image cannot

currently be displayed.

Lewis
structure

This image cannot

currently be
displayed.

3D representation

space-filling
representation

This image cannot currently be displayed.

two primary carbons and two secondary carbons.

75

C4H10

CH3
H3C C CH3
H
the central carbon is a tertiary carbon.
2-methyl-propane

76

CH3-H = methane
CH3- = methyl
CH3-CH3 = ethane
CH3-CH2- = ethyl
CH3-CH2-CH3 = propane
CH3-CH2-CH2- = propyl
CH3-CH2-CH2-CH3 = butane
CH3-CH2-CH2-CH2- = butyl
77

IUPAC
International Union of Pure
and Applied Chemistry

78

IUPAC SYSTEM OF NAMING COMPOUNDS

1. Select the longest continuous chain of carbon atoms for
the basic name.
2. Number the carbons in the chain from the end nearest the
first branch.
3. Identify substituents (e.g. methyl, ethyl, bromo, chloro). If
more than one substituent of the same kind is present, use
the prefixes di, tri or tetra.
4. Locate the substituents by the number of the carbon to
which they are attached.
5. Put substituents in alphabetical order (prefixes (di, tri,
tetra, n-, sec-, tert-, do not count).
6. Use commas to separate numbers and separate numbers
from letters by a dash and write the whole name as one word
79
with the basic name at the end.

H3C

H2
C
5

CH3
4

CH

C
H2

C
H2

CH3
1

3-methylhexane
80

CH3
CH3CHCH2CH2CH3
1

22

33

44

55

pentane
2-methylpentane
81

CH3CH3

CH2CH3

CH3CHCHCH2CHCH2CH2CH3
1

decide longest chain

number the carbon atoms
82

CH3CH3

CH2CH3

CH3CHCHCH2CHCH2CH2CH3
1

5-ethyl-2,3-dimethyloctane
83

CH3CH3

CH2CH3

CH3CHCHCH2CHCH2CH2CH3
1

5-ethyl-2,3-dimethyloctane
84

CH3CH3

CH2CH3

CH3CHCHCH2CHCH2CH2CH3
1

5-ethyl-2,3-dimethyloctane
85

H3C
CH
H3C
1

CH2
2

CH2

H3C

CH3
3

5 CH2

CH
5

H2C

CH2
7 CH3

H3C

CH3

CH
CH

CH2

H3C

In finding the longest straight chain of carbons,

it is often necessary to count around corners.
The chain is numbered so as to produce the
smallest number for a substituent.

heptane
3,4-dimethylheptane

86

8
7
5
4

6
3

2
1

octane
3,5-dimethyloctane
4-ethyl-3,5-dimethyloctane

87

4
nonane

3-methyl

nonane

3-methyl-4-propylnonane

88

line structure

hexane
tetramethylhexane
2,2,3,4-tetramethylhexane
89

 Number chain to make substituent locator numbers

as low as possible

90

What is the IUPAC name of the following compound?

A) 2,3-dimethyloctane
B) 2,3,6-trimethylheptane
C) 2,3,6-methylheptane
D) 2,5,6-trimethylheptane
E) both B and D

Provide an IUPAC name for the following:

H3C
H

CH3

CH2CH2CH3

H
CH2CH3

A) 4-ethyl-4-methylhexane
B) 2,2-diethylpentane
C) 3-ethyl-3-methylhexane
D) 3-methyl-3-propylpentane

Cycloalkanes

H
H
H

H
C

C
C
H

C
C

C
H

H
H

Cycloalkanes are cyclic hydrocarbons with the general formula CnH2n

94

Representations of cyclohexane
H

H
H

H
H

H
H

H
C

C
C
H

C
C

C
H

H
H

3D structure

line structure

95

Cycloalkanes

General formula CnH2n.

five- and six-membered rings are the most common.

Structure and nomenclature.

to name, prefix the name of the corresponding open-chain
alkane with cyclo-, and name each substituent on the ring.
if only one substituent, no need to give it a number.
if two substituents, number from the substituent of lower
alphabetical order.
if three or more substituents, number to give them the lowest
set of numbers and then list substituents in alphabetical
order.

CH3

methylcyclohexane
97

Br
1-bromo-3-tert-butylcyclohexane
1-bromo-3-t-butylcyclohexane
98

ALKENES & ALKNES

100

IUPAC functional groups

HC CH

CH2=CH-CH3

eth-yn-e = ethyne

prop-en-e = propene

CH 3 CH 2 CH 2 CH

CH 3 CCH 2 CH 3
but-an-one = butanone

but-an-al = butanal

OH

CH 3 CH 2 CH 2 CH 2 COH
pent-an-oic acid = pentanoic acid
CH3-CH2-NH2
eth-an-amine = ethanamine

cyclohex-an-ol = cyclohexanol
CH3-CH2-OH
eth-an-ol = ethanol

IUPAC SYSTEM OF NAMING ALKENES

1. Select the longest continuous chain of carbon atoms
which contains both carbons of the double bond for the
basic name.
2. Change the ending to ene from the ane of the
corresponding alkane.
3. Number the carbons in the chain from the end nearest the
first carbon of the double bond.
4. Locate the position of the double bond by the number of
the first carbon involved in the double bond.
5. Name substituents as with alkanes.
6. In a cyclic system number the carbons of the double
bond as 1 and 2.
102

CH3
CH3CH2CH CHCH2CHCH3

heptene
3-heptene
6-methyl-3-heptene
or 6-methylhept-3-ene
103

1-butene or but-1-ene
1,3-butadiene or buta-1,3-diene
3

3-methyl-1,3-heptadiene
2

3-propyl-1-nonene
104

1-methylcyclohexene
3
2

3-methylcyclohexene

2
1

2-methyl-1,3-cyclohexadiene

105

Nomenclature - alkyne

H
C
C
H

acetylene

106

Nomenclature - alkyne

CH3
H
C
C
H

IUPAC propyne

107

Nomenclature - alkyne
If you have both double and triple bonds in a
compound, you number from the end nearest
the first multiple bond. If there is a choice,
double bonds get lower numbers than triple
bonds.

HC CCH2CH2CH=CH2
1- hexene-5-yne
108

IUPAC SYSTEM OF NAMING ALKYNES

1. Select the longest continuous chain of carbon atoms
which contains both carbons of the triple bond for the
basic name.
2. Change the ending to yne from the ane of the
corresponding alkane.
3. Number the carbons in the chain from the end nearest the
first carbon of the triple bond.
4. Locate the position of the triple bond by the number of the
first carbon involved in the triple bond.
5. Name substituents as with alkanes.
6. In a cyclic system number the carbons of the triple bond
as 1 and 2.
7. Double bonds have priority over triple bonds.

109

H
C
3

1
CH
3

H
C
3

1-butyne or but-1-yne
not 3-butyne

2-methyl-2-hexene-4-yne
or 2-methylhex-2-ene-4-yne
not 5-methyl-4-hexen-2-yne

CH
3

HC

CH
3

CH
3

3,3-Dimethyl-1-butyne
110