Hydrocarbon PDF

LET’S REVIEW
Game rule:
• You are given 10 seconds to
decide your answer.
Question 1
Prefix
Hept—
Question 2
Hydrocarbon
Question 3
suffix
—ane
Question 4
H H
ǀ ǀ
H─C ─C─H
ǀ ǀ
H H
Question 5
Isopropyl
Question 6
CH3−CH2−CH−
ǀ
CH3
OUR GOALS
1. Explain about special characteristics of carbon atom.
2. Determine the aliphatic, alicyclic, and aromatic based on hydrocarbon chain.
3. Differ atom of C primary, secondary, tertiary and quarternary .
4. Interpret and use the chemical names, general formulae and displayed formulae of
alkane, alkene and alkyne.
5. Explain the relationship between boiling point of hydrocarbon and its structure.
6. Explain the isomer of hydrocarbon based on its structure (chain and position) and
geometry ( cis and trans).
7. Write down simple reaction of alkane, alkene, and alkyne (oxidation, addition,
substitution, and elimination reaction)
Organic compound
(Carbon compound)
• All living things made of organic compound.
Carbohydrate
Lipid
Protein
Nucleic acid
Special Characteristics of Carbon Atom
1. Forms 4 covalent bonds (bond to itself or many
different atoms).
2. The carbon atoms in a chain can be linked by single,
double or triple covalent bond.
3. Forms chains, branches and rings.
4. The electrons that are not being used to bond carbon
atoms together into chains and rings can be used to
form bonds with atoms of several other elements.
Allotropes of Carbon
a. Diamond
b. Graphite
c. Lonsdaleite
d-f. Fullerene (C60 ,
C540 , C70)
g. Amorphous carbon
h. Carbon nanotube
Hydrocarbon
a compound that contains
hydrogen and carbon only.
Open chain compound Close chain

(Aliphatic) compound
Saturated Unsaturated alicyclic

Aromatic
Alkyne
(alkane) Alkene
Aliphatic
open chain compounds
Propane
Propene
Propyne
Alicyclic
closed chain compounds
Aromatic-alicyclic
consist of one or more rings that contain alternating single
and double bonds in its chemical structure.
Benzene
Position of carbon atom
Primary (C1°), Secondary (C2°), Tertiary (C3°), and Quaternary (C4°)
Classify each carbon atom!
Home
ALKANE
RiinSandrayanti/IBCSHS/2019 20
Alkane ( − )
• Hydrocarbon with general formula CnH2n+2
• Contain only single covalent bonds between carbon atoms.
Alkane, CnH2n+2
Number of C Prefix Formula Alkane
atom
CH4 methane
1 Meth-
C2H6 Ethane
2 Eth-
C3H8 Propane
3 Prop-
Butane
4 But-
Pentane
5 Pent-
Hexane
6 Hex-
7 Hept- Heptane
8 Oct- Octane
9 Non- Nonane
10 Dec- Decane
HOMOLOGOUS SERIES
1. Similar chemical properties, CH3—CH2—CH3

2. Same general formula,
3. Members differ by one −CH2− unit,
CH3—CH2—CH2—CH3
4. Show a gradual increase in physical properties
such as boiling point and melting point.
Displayed formulas of Alkanes
Alkane Displayed formula Alkane Displayed formula
CH4 H C4H10
ǀ
H−C−H
ǀ
H
C2H6 H H
ǀ ǀ
C5H12
H─C ─C─H
ǀ ǀ
H H
C3H8 H H H
ǀ ǀ ǀ
C6H14
H─C ─C─C─H
ǀ ǀ ǀ
H H H
Some important terms
Naming hydrocarbon
compounds
Write the substituent first
Find the parent Give number and
alphabetically and follow
chain find substituent
by parent’s name
Nomenclature of Alkane based on IUPAC
1. Find the longest continuous chain (parent chain) of carbon atoms. This longest
chain may not be written in a straight line.
CH2−CH3
ǀ
CH3−CH2−CH−CH−CH2−CH3
ǀ
CH3
2. Name that longest chain with the appropriate alkane name.
3. Find the substituents (alkyl) and name each of them with the appropriate group
name.
Substituents or Alkyl, CnH2n+1
Alkane Formulae Alkyl Formulae
Methane CH4 Methyl CH3
Ethane C2H6 Ethyl C2H5
Propane C3H8 Propyl C3H7
Butane C4H10 Butyl C4H9
Pentane C5H12 Pentyl C5H11
Hexane C6H14 ... ...
Heptane C7H16 ... ...
Common branched substituents which you
should memorize.
Branches Structure Branches Structure
Isopropyl CH3− CH− Secondary butyl CH3−CH2−CH−
ǀ (sec-butyl) ǀ
CH3 CH3
Isobutyl CH3−CH−CH2− Tertiary butyl CH3

ǀ (t-butyl) ǀ
CH3 CH3− C −
ǀ
CH3
4. Number the carbons in the chain such that the lowest number is given to the alkyl
nearest one end of the chain. If two or more alkyls are in equivalent positions,
assign the lowest number to the one which will come first in the name.
CH2−CH3
ǀ
ǀ
CH3
5. List the alkyls alphabetically in front of the longest chain name.
30
RiinSandrayanti/IBCSHS/2019
6. Precede each alkyl name with a prefix indicating how many of them are present
in the molecule. In front of the prefix, list the numbers of each group in the
molecule and separate the numbers with a hyphen (‒).
CH3 CH2−CH3
ǀ ǀ
6 5 4 3 2 1
7. If the same alkyls occurs more than once, the location of each point on which
the alkyls occurs is given. In addition, the number of times the alkyls group
occurs is indicated by a prefix (di, tri, tetra, etc.).
8. If there are two or more different alkyls they are listed in alphabetical order
using the base name (ignore the prefixes). The only prefix which is used when
putting the alkyls in alphabetical order is iso as in isopropyl or isobutyl. The
prefixes sec- and tert- are not used in determining alphabetical order
except when compared with each other.
CH3 CH3
ǀ ǀ
CH3−CH−CH2−CH2−CH−CH2−CH−CH2−CH3
ǀ
CH−CH3
ǀ
CH2−CH3
9. If chains of equal length are competing for selection as the parent chain, then the choice goes in
series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents/alkyls have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in the smaller side chain.
d) the chain having the least branched side chains.
CH3 ‒ CH2 ‒ CH ‒ CH ‒ CH ‒ CH ‒ CH3 CH3 ‒ CH2 ‒ CH ‒ CH ‒ CH ‒ CH ‒ CH3

ǀ ǀ ǀ ǀ ǀ ǀ ǀ ǀ
CH3 CH2 CH3 CH3 CH3 CH2 CH3 CH3
ǀ ǀ
CH2 CH2
ǀ ǀ
CH3 CH3
10. A cyclic (ring) hydrocarbon is designated by the
prefix cyclo- which appears directly in front of the
base name.
11. The name of the compound is written out with the cyclopropane
substituents in alphabetical order followed by the
base name (derived from the number of carbons in
the parent chain). Commas are used between
numbers and dashes (-) are used between letters and
numbers. There are no spaces in the name.
cyclobutane
Examples
1 2 3 4
2-methylbutane
4 3 2 1
CH3 CH2 CH CH2 CH2 CH3
CH2 CH2 CH3

5 6 7
4-ethylheptane
CH2 CH3
CH3 CH2 CH2 CH CH CH2 CH3

7 6 5 4 3 2 1
CH3
4-ethyl-3-methylheptane
CH3
CH3 CH CH CH3
1 2 3 4
CH3
2,3-dimethylbutane
CH3 CH3
CH3 CH CH2 C CH3

5 4 3 2 1
CH3
2,2,4-trimethylpentane
Alkene ( ═ )
• Hydrocarbon with general formula, CnH2n
• Contain one or more double bond between carbon
atoms.
• Replace –ane with –ene.
Alkane Formulae Alkene Formulae
ethane C2H6 Ethene C2H4
propane C3H8 Propene C3H6
butane C4H10 butene C4H8
Alkene, CnH2n
Formulae Alkene Structure

C2H4 Ethene CH2 ═ CH2
C3H6 Propene CH3−CH ═ CH2
C4H8 Butene CH3−CH2−CH ═ CH2
Pentene CH3−CH2−CH2−CH ═ CH2
Hexene
Heptene
Octene
Nonene
Decene
Alkyne ( ≡ )
• Hydrocarbon with general formula, CnH2n-2
• Contain one or more triple bond between carbon
atoms.
• Replace –ane with -yne.
Alkane Formulae Alkyne Formulae

ethane C2H6 Ethyne C2H2
propane C3H8 Propyne C3H4
butane C4H10 Butyne C4H6
Formulae Alkyne Structure
C2H2 Ethyne CH ≡ CH
C3H4 Propyne CH3−C ≡ CH
C4H6 Butyne CH3−CH2−C ≡ CH
Pentyne CH3−CH2−CH2−C ≡ CH
Hexyne
Heptyne
Octyne
Nonyne
Decyne
Naming Alkene and Alkyne
1. Find the longest continuous chains that contain double and triple bond as a
parent chain.
2. Number the parent chain so that double and triple bond have the lowest
numbers (double and triple bonds have priority over alkyl).
3. List the alkyls alphabetically in front of the longest chain name.
4. Precede each alkyl name with a prefix indicating how many of them are present
in the molecule. In front of the prefix, list the numbers of each group in the
molecule and separate the numbers with a hyphen (-).
Special rules
5. If more than one double bond is present, the prefixes di-, tri-, tetra-, etc. are used before the
-ene, and (strangely) the letter "a" is added after the parent chain’s prefix.
6. When both double and triple bonds are present:
– Alkenes and alkynes are considered to have equal priority
– Whichever is closer to the end of the chain determines the direction of numbering
– In the case where each would have the same position number, the double bond takes the lower number
– In the name, ‘ene’ comes before ‘yne’ because alphabetization.
3,5-dimethyl-3-hexen-1-yne
7. When both double and triple bonds are present, the -en suffix follows the parent chain
directly and the -yne suffix follows the -en suffix (notice that the e is left off, -en instead of
-ene). The location of the double bond(s) is(are) indicated before the parent name as
before, and the location of the triple bond(s) is(are) indicated between the -en and -yne
suffixes. See below for examples.
CH ≡ C −CH ═ CH−CH ═ CH2

1,3-hexadien-5-yne
8. If there is a choice in numbering not previously covered, the parent chain is
numbered to give the substituents the lowest number at the first point of
difference.
CH3
ǀ
CH3−CH−C ═ CH−CH−CH3
ǀ ǀ
CH3 CH3
Examples
1. CH3−CH ═ CH−CH2−CH−CH3
ǀ
CH3
2. CH2 – CH3
ǀ
CH3─ CH2─ C = CH ─ CH3
3. CH3─ CH2─ C  C ─ CH3 5. CH2 ═ CH−CH2−CH ═ CH−CH3
4. CH3─ CH─ C  C ─ CH3 6. CH3−CH ═ CH−C ≡ CH

ǀ
CH−CH3
ǀ
CH3 7. CH3− CH − C ═ CH−CH−CH3
ǀ ǀ ǀ
CH3 C2H5 CH3
Draw the display structural formula of :
a. 2,2-dimethylbutane
b. 2,2,4-trimethylpentane
c. 4,4-dimethyl-2-hexene
d. 4-ethyl-4-methyl-2-heptyne
e. 5,5-dimethyl-1-hexyne
f. 1,4,4-trimethylcyclobutene
ISOMERISM of Hydrocarbon compounds
Isomers are
molecules that have
the same molecular
formula, but have a
different
arrangement of the
atoms in space.
Structural Isomerism
1. Branched Chain, example :
Isomers of C7H16
1. n-heptane 6. 2,4-dimethylpentane
2. 2-methylhexane 7. 3,3-dimethylpentane
3. 3-methylhexane 8. 3-ethylpentane
4. 2,2-dimethylpentane 9. 2,2,3-trimethylbutane
5. 2,3-dimethylpentane
2. Position Isomerism, for alkene and alkyne only--
movement of (═) and (≡).
Examples :
CH3 − CH2 − CH2 − CH ═ CH2
1-pentene or pent-1-ene
CH3 − CH2 − CH ═ CH2 − CH2
2-pentene or pent-2-ene
Isomers of C6H12
1. 1-hexene 11. 2,3-dimethyl-1-butene
2. 2-hexene 12. 3,3-dimethyl-1-butene
3. 3-hexene 13. 2-ethyl-1-butene
4. 2-methyl-1-pentene
10. 2,3-dimethyl-2-butene
Isomers of C6H10
1. 1-hexyne
2. 2-hexyne
3. 3-hexyne
4. 3-methylpentyne
5. 4-methylpentyne
6. 4-methyl-2-pentyne
7. 3,3-dimethyl-1-butyne
Isomer C5H10
1. 1-pentene
2. 2-pentene
3. 2-methyl-1-butene
Stereoisomerism
1. Geometry
Cis-2-butene Trans-2-butene
2. Optical (Chiralty), occurs when there is an asymmetric
carbon (C has 4 different atom or group attached).
Example
Example
Chiral
H
ǀ
H3C− CH2− C −CH2−CH2−CH3
ǀ
CH3
Label the C chiral
CH3 CH2 −CH3

ǀ ǀ
CH3 −CH−CH−C−CH3
ǀ ǀ
CH2 CH3
ǀ
CH3
Physical Properties of Alkanes (—),
Alkenes ( ═ ), and Alkynes ( ≡ )
• Melting point and boiling point increase when the molecular size increases. The
larger molecular size, the stronger the Van Der Waals forces of attraction
between molecules. Thus more energy is needed to overcome the forces
attraction during melting or boiling.
• Less dense than water.
• Insoluble in water but soluble in organic solvent.
• Colorless
• Can not conduct electricity
Physical Properties of Alkane, Alkene, &
Alkyne
• Boiling point
increase with number of carbons.
Alkane b.p Alkene b.p Alkyne b.p
(°C) (°C) (°C)
Ethane -89 Ethene -104 Ethyne -84
Propane -42 Propene -47 Propyne -23
Butane 0.5 Butene -7 Butyne 8
Pentane 36 Pentene 30 Pentyne 40
b.p trends : alkyne > alkane> alkene

• The boiling points of the alkanes, alkenes, and alkynes
increases with molecular size.
• The longer the chains, the higher the b.p.
• Van der waals dispersion forces get bigger when the
molecular size increases.
• The more branched the chain, the lower the boiling point
tends to be. Van der Waals dispersion forces are smaller for
shorter molecules
Why alkynes has the highest b.p than
alkanes and alkenes ? And why
alkenes has the lowest b.p?
Some factors affected Van Der Waals
forces (LDF)
• Molecular mass (size of the molecules)
• Shape of the molecules (surface area)
• Bond length
• Electron Density
Alkyne has the highest boiling point
than others with the same number of
carbon, because:
• Triple bonds are the shortest. (137 pm). Correlation
between bond length and bond strength; shorter
the bond the stronger it is.
• It has branching limit that makes the surface area
bigger.
Alkanes has higher boiling point than
alkenes with the same number of
carbon because:
• Alkanes have the longest C-H bond (154 pm).
• Alkene have shorter C-H bond than alkane which is 147 pm. A
double bond (although stronger because it is shorter) is not twice
as strong as a single bond! This is because the pi bond is not as
strong as the sigma bond.
• Alkanes has 2 more electrons than alkenes so the electron
density is increased. The higher the electron density, the stronger
the LDF.
Why Alkyne has higher boiling point
than alkane if alkyne has less electron
density than alkane in the molecule
with equal number of carbon?
• Because the effect of branching and the attractive
force between carbon atom in alkynes is more
effective than electron density.
• For examples, the boiling points of three isomers of
C5H12 are :
CHEMICAL Properties of Alkane, Alkene,
& Alkyne
1. In general alkane have a low reactivity, the most important
reaction are combustion (reaction with oxygen) and halogenation
(reaction with halogen)-substitution.
2. Alkene and alkyne are more reactive than alkane.
3. The most characteristic reaction of alkene and alkyne is addition.
Reaction of Alkane
1. Combustion –reaction with
oxygen
• In this reaction, CO2, H2O, and heat (energy)
are produced.
CH4 + 2O2 → CO2 + 2H2O + energy
turns cloudy
Turns red
2. Substitution reaction-halogenation
• A substitution reaction occurs when one atom of an organic molecule is replaced by

another atom.
• Substitution reactions often require heat and/or a catalyst in order to occur.
• Alkanes react with chlorine and bromine if we heat the mixture or if we expose the
mixture to light (in the dark at room temperature, nothing happens).
If chloromethane is allow to react with more
chlorine
Reaction of Alkene and Alkyne
•Addition
is a reaction in which two molecules join together to make a bigger one.
There are 4 types of addition :
1. Addition of hydrogen (hydrogenation)
2. Addition of water (hydration)
3. Addition of hydrogen halide (hydrohalogenation)
4. Addition of chlorine and bromine (halogenation)
1. Addition of hydrogen
(Hydrogenation)-reduction
• A catalyst as platinum (Pt), Nickel (Ni), or palladium (Pd) is added to
speed up the reaction.
• Alkene → alkane
• Alkyne → alkene → alkane
2. Addition of water
(Hydration)
• Use in the manufacture of ethanol-important chemical and solvent.
• A catalyst of immobilized phosphoric (V) acid (the acid is absorbed on a silica
pellets).
300°C
Steam
3. Addition of hydrogen halide
(Hydrohalogenation)
• Hydrogen halide (HX ex: HCl, HBr, HI)
H H H Cl
ǀ ǀ ǀ ǀ
C═C + H−Cl →H−C−C−H
ǀ ǀ ǀ ǀ
H H H H
Markonikov’s rule
• …the more electronegative (for example negative ion) atom
will predominantly bond to the carbon atom of the double
bond that has fewer hydrogen atoms.
Example
4. Addition of halogen-Halogenation
(Cl2, Br2, I2)
• No catalyst needed
• Can react at room temperature
• Use dichloromethane as a solvent
Elimination Reaction
• Is a method for preparation of alkenes by :
1. Dehydration from alcohols
2. Dehydrohalogenation of alkyl halides or halogenoalkanes
(hydrocarbon compound that contain halide, Cl, Br, or I)
Zaytzeff’s Rule
• If more than one elimination product is possible, the most
substituted alkane is the major product (most stable).
1. Dehydration from alcohol (water is
produced)
Alcohols can undergo elimination via the loss of water.
This is known as dehydration.
H H
ǀ ǀ Acid, heat
H − C − C −H H2C = CH2 + H2O
ǀ ǀ
H OH RiinSandrayanti/IBCSHS/2019 89
2. Dehydrohalogenation (halide (Cl-, Br-, I-) is
produced)
• Strong base like KOH (alcoholic) is used.
KOH(alc)
KBr

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LET’S REVIEW

• All living things made of organic compound.

d-f. Fullerene (C60 ,

Open chain compound Close chain

Saturated Unsaturated alicyclic

1. Similar chemical properties, CH3—CH2—CH3

Isobutyl CH3−CH−CH2− Tertiary butyl CH3

CH3 ‒ CH2 ‒ CH ‒ CH ‒ CH ‒ CH ‒ CH3 CH3 ‒ CH2 ‒ CH ‒ CH ‒ CH ‒ CH ‒ CH3

CH2 CH2 CH3

CH3 CH2 CH2 CH CH CH2 CH3

CH3 CH CH2 C CH3

propane C3H8 Propene C3H6

butane C4H10 butene C4H8

Formulae Alkene Structure

Alkane Formulae Alkyne Formulae

propane C3H8 Propyne C3H4

butane C4H10 Butyne C4H6

CH ≡ C −CH ═ CH−CH ═ CH2

4. CH3─ CH─ C  C ─ CH3 6. CH3−CH ═ CH−C ≡ CH

CH3 − CH2 − CH ═ CH2 − CH2

CH3 CH2 −CH3

b.p trends : alkyne > alkane> alkene

CH4 + 2O2 → CO2 + 2H2O + energy

• A substitution reaction occurs when one atom of an organic molecule is replaced by

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