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 Mechanisms

nomenclature 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 2
 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
 sp2 Hybrid Orbitals
One pure s orbital Two pure p orbitals

Three hybrid sp2 atomic

orbitals

4
 3 hybrid sp2 orbitals

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).
5
Consider ethylene, C2H4: H H

The Lewis structure is: C C

H H

 2pz 2pz (C2pz, C2pz)
sp2 sp2
H H
C C C C
sp2 sp2 H H
sp2 sp2
 (Csp2, H1s)

(Csp2, Csp2)

2p 2pz

2s hybridize sp2

1s 1s
s + px + py
ground state of C sp2 hybridized carbon
6
 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.

7
 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). 8
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.

9
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 H H
C C C 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
O
 
C
σ σ
H3C CH3

non-bonded pairs: n
11
 sp Hybrid Orbitals

s + p = 2 sp z
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° apart, as well as two
perpendicular p orbitals.
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 2p

2s hybridize sp

1s 1s
s + pz
ground state of C 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 C≡C triple bond is made up of one  bond and two  bonds.

The bond energies (strenghts) are: E(C≡C) > 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

sp C C alkynes
sp3 OH alcohols

sp C N nitriles
sp3 R O R ethers

sp2 C C alkenes
O
O sp2 C carboxylic acids
sp2 C ketones R OH
R R O
O sp2 C esters
sp2 C aldehydes R OR
R H 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 Å 25%s & 25%s

Csp3-Csp2 single bond 1.50 Å 25%s & 33%s
Csp3-Csp single bond 1.46 Å 25%s & 50%s

shorter bonds are also stronger bonds.

C≡C strength > C=C strength > C-C strength

21
BOND STRENGTHS - MULTIPLE BONDS
CC bond bond bond energy molecule
bond type length per mole measured

Kcal (KJ)

C-C sp3-sp3 1.54 A 83 (347) CH3CH3

C=C sp2-sp2 1.34 A 146 (611) CH2=CH2

C≡C sp - sp 1.20 A 200 (837) HC≡CH

22
BOND STRENGTHS - MULTIPLE BONDS
CC bond bond bond energy molecule
bond type length per mole measured

Kcal (KJ)

C-C sp3-sp3 1.54 A 83 (347) CH3CH3

C=C sp2-sp2 1.34 A 146 (611) CH2=CH2

C≡C sp - sp 1.20 A 200 (837) HC≡CH

stronger
shorter
increasing
s-character

Typical pi bonds have a bond

energy of about 50-60 kcal/mole
23
 Orbitals and stability (C6H12)
H3C CH3 H3C H2C CH3 H H2C CH3 H2C CH3
C C C C C C H H2C CH2
H3C CH3 H3C H H3C CH2 H C 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
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 carbon-
carbon 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 carbon-

hydrogen 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 H
H
C C
H H 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 H
H
C C
H H 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 H
H
C C
H H 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 H
H
C C
H H 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
 H -60° dihedral angle
HH 0° dihedral angle
H H

H H H H
H H
H

staggered conformation 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
 H 60° dihedral angle
HH 0° dihedral angle
H H

H H H H
H 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
 HH
consider butane HH
C H
C
C C
CH3CH2CH2CH3 H
HH HH

CH3 The most stable conformation has a

H H dihedral angle of 180° between
the methyl groups.
H H
This staggered conformation is
CH3
called the anti-conformation
48
 HH
consider butane HH
C H
C
C C
CH3CH2CH2CH3 H
HH HH

CH3
H H

H H
CH3

49
 Butane, CH3CH2CH2CH3
CH3 CH3
H CH3 H3C H

H 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 60º?

A) CH3 B) H3C
H CH3 H CH3
H

H H
C) H D) H H

CH3 H
H H H CH3

H H H H
CH3 CH3
 Hydrocarbons
space-filling models
Alkanes have the general formula CnH2n+2

1 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

straight-chain branched-chain

CH2 CH3
CH3
CH2 CH2 H3C C
H3C CH2 CH3 C
CH3
H CH3 H3C
CH3

n-pentane 2-methylbutane 2,2-dimethylpropane

bp 36.1 °C bp 27.9 °C bp 9.5 °C
mp -129.7 °C mp -159.9 °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

Molecular Constitutional
Formula Isomers
CH4 1
C5 H1 2 3
C1 0 H2 2 75
C1 5 H3 2 4,347
C2 5 H5 2 36,797,588
C3 0 H6 2 4,111,846,763

67
 Nomenclature - IUPAC
 Suffix -ane specifies an alkane
 Prefix tells the number of carbon atoms

Prefix Carbons Prefix Carbons

meth- 1 undec- 11
eth- 2 dodec- 12
prop- 3 tridec- 13
but- 4 tetradec- 14
pent- 5 pentadec- 15
hex- 6 hexadec- 16
hept- 7 heptadec- 17
oct- 8 octadec- 18
non- 9 nonadec- 19
dec- 10 eicos- 20
68
 methane, CH4

H
H H
CH4 H C H C
H
HH
condensed Lewis 3D representation space-filling
formula structure 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
This image cannot currently be display ed.

CH3CH3

condensed Lewis
formula structure

All hydrogen atoms in ethane are equivalent

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:

H Cl Cl Cl
C C C C
HH HCl HH HH

1,1-dichloroethane 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

H H
H H H
CH3CH2CH3
H C C C H H C C H
H C H
H H H HH

condensed Lewis 3D representation space-filling

formula structure 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

CH3CH2CH2CH3

condensed
formula

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.
 CH3
H2
6 C 4 CH 2 CH3
5 1
H 3C C 3
C
H2 H2

3-methylhexane
80
 CH3
CH3CHCH2CH2CH3
11 22 33 44 55

pentane
2-methylpentane
81
 CH3CH3 CH2CH3
CH3CHCHCH2CHCH2CH2CH3
1 2 3 4 5 6 7 8

decide longest chain

number the carbon atoms
82
 CH3CH3 CH2CH3
CH3CHCHCH2CHCH2CH2CH3
1 2 3 4 5 6 7 8

5-ethyl-2,3-dimethyloctane

83
 CH3CH3 CH2CH3
CH3CHCHCH2CHCH2CH2CH3
1 2 3 4 5 6 7 8

5-ethyl-2,3-dimethyloctane

84
 CH3CH3 CH2CH3
CH3CHCHCH2CHCH2CH2CH3
1 2 3 4 5 6 7 8

5-ethyl-2,3-dimethyloctane

85
 7 6
H3C CH2
H 3C CH3
3 4 5 CH2
CH CH 4 1
5 6 H3C CH CH3
H3C CH2 H2C CH2
1 2 CH CH2
7 CH3 3 2
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

6
5
4 2
3
1

octane
3,5-dimethyloctane
4-ethyl-3,5-dimethyloctane 87
 2
3 1

9 8 7 6 5 4

nonane

3-methyl nonane

3-methyl-4-propylnonane

88
 line structure

6 5 4 3 2
1

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:

CH3
H3 C CH2CH2CH3

H 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 H
H C C H
C
H H
H H

Cycloalkanes are cyclic hydrocarbons with the general formula CnH2n

94
 Representations of cyclohexane

H H
H H H H
H C
H H
C C
H
H H
H C C H
H H C
H H H
H H
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
CH2=CH-CH3 HC CH

prop-en-e = propene eth-yn-e = ethyne

O O
CH3 CCH2 CH 3 CH3 CH2 CH2 CH
but-an-one = butanone but-an-al = butanal

O OH
CH3 CH2 CH2 CH2 COH
pent-an-oic acid = pentanoic acid cyclohex-an-ol = cyclohexanol

CH3-CH2-NH2 CH3-CH2-OH
eth-an-amine = ethanamine 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
1 2

1
2 3-propyl-1-nonene
104
 1-methylcyclohexene

3
2
3-methylcyclohexene
1

2
3
1
2-methyl-1,3-cyclohexadiene

105
Nomenclature - alkyne

H-C C-H

acetylene

106
 Nomenclature - alkyne

H-C C-H
CH3

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
6 5 4 3
H3C C C C
1 1
2
CH3
H3C

1-butyne or but-1-yne 2-methyl-2-hexene-4-yne

not 3-butyne or 2-methylhex-2-ene-4-yne
not 5-methyl-4-hexen-2-yne

CH3
1 3
HC C C CH3

CH3

3,3-Dimethyl-1-butyne

110