CHEM331 Organic Chemistry (3 CR.) : Fall 2020 2021

11/19/2020
CHEM331 ‐ Organic Chemistry (3 cr.)
Fall 2020‐2021
Course Instructor: Jean El Achkar, PhD, Assistant Professor
E‐mail: j.achkar@bau.edu.lb
Chapter 3: Alkanes
ORGANIC CHEMISTRY FUNCTIONAL GROUPS
H, C, HALOGENS H, C, O
H, C
ALKYL HALIDE ALCOHOLS & PHENOLS

ETHER & EPOXIDE
BENZENE
ALDEHYDE & KETONE
CARBOXYLIC ACID
ALKANES
ALKENES
ALKYNES
ALIPHATIC CYCLIC AROMATIC
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Functional Groups with Carbon Singly Bonded to an Electronegative
Atom
• Alkyl halide: C bonded to halogen (C‐X)
• Alcohol: C bonded O of a hydroxyl group (C‐OH)
• Ether: Two C’s bonded to the same O (C‐O‐C)
• Amine: C bonded to N (C‐N)
• Thiol: C bonded to SH group (C‐SH)
• Sulfide: Two C’s bonded to same S (C‐S‐C)
• Bonds are polar, with partial positive charge on C (+) and partial negative charge
() on electronegative atom
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Groups with a Carbon–Oxygen Double Bond (Carbonyl Groups)
• Aldehyde: one hydrogen bonded to C=O
• Ketone: two C’s bonded to the C=O
• Carboxylic acid: ‐OH bonded to the C=O
• Ester: C‐O bonded to the C=O
• Amide: C‐N bonded to the C=O
• Acid chloride: Cl bonded to the C=O
• Carbonyl C has partial positive charge (+)
• Carbonyl O has partial negative charge (‐).
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Alkanes and Alkane Isomers
• Alkanes: Compounds with C‐C single bonds and C‐H bonds
only (no functional groups)
• The formula for an alkane with no rings (acyclic) must be
CnH2n+2 where the number of C’s is n
• Alkanes are saturated with hydrogen (no more can be
added)
• They are also called aliphatic compounds
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Alkane Isomers
• CH4 = methane, C2H6 = ethane, C3H8= propane
• The molecular formula of an alkane with more than three carbons can
give more than one structure
• C4 (butane) = butane and isobutane
• C5 (pentane) = pentane, 2‐methylbutane (isopentane), and 2,2‐
dimethylpropane (neopentane)
Methane, ethane, & propane
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Butanes (C4H10):
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Pentanes (C5H12):
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Alkane
Isomers
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Alkane Isomers
• Alkanes with C’s connected to no more than 2
other C’s are straight‐chain or normal alkanes
• Alkanes with one or more C’s connected to 3 or 4
C’s are branched‐chain alkanes
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Constitutional Isomers
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Names of Small Hydrocarbons
No. of Carbons Formula Name (CnH2n+2)
1 Methane CH4
2 Ethane C2H6
3 Propane C3H8
4 Butane C4H10
5 Pentane C5H12
6 Hexane C6H14
7 Heptane C7H16
8 Octane C8H18
9 Nonane C9H20
10 Decane C10H22
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Alkyl Groups
• Alkyl group – remove one H from an alkane (a part of a
structure)
• General abbreviation “R” (for Radical, an incomplete species
or the “rest” of the molecule)
• Name: replace ‐ane ending of alkane with ‐yl ending
• ‐CH3 is “methyl” (from methane)
• ‐CH2CH3 is “ethyl” from ethane
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Alkyl Groups
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Types of Alkyl groups
• a carbon at the end of a chain (primary alkyl group)
• a carbon in the middle of a chain (secondary alkyl
group)
• a carbon with three carbons attached to it (tertiary
alkyl group)
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Types of Carbon Atoms
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Types of Hydrogens:
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Nomenclatures of alkanes: use the IUPAC system
RULE 1: THE MAIN CHAIN

The first rule of nomenclature gives the base name of the compound.
Find the longest continuous chain of carbon atoms and use the name of this chain as
the base name of the compound.
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RULE 1: THE MAIN CHAIN

The first rule of nomenclature gives the base name of the compound.
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RULE 2: NUMBERING THE MAIN CHAIN

To give the locations of the substituents, assign a number to each carbon atom on the
main chain.
Number the longest chain, beginning with the end of the chain nearest a substituent.
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RULE 3: NAMING ALKYL GROUPS Name the substituent groups.
Name the substituent groups attached to the longest chain as alkyl groups. Give the
location of each alkyl group by the number of the main‐chain carbon atom to which it
is attached.
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Atom/ Group Name as substituent
Of atoms
Fluorine fluoro‐
Chlorine chloro‐
Bromine Bromo‐
Iodine Iodo‐
NO2 Nitro‐
NH2 Amino‐
CN Cyano‐
Cyclo Cyclo‐
Phenyl Phenyl‐ 29
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RULE 4: ORGANIZING MULTIPLE GROUPS

The final rule deals with naming compounds with more than one substituent.
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Physical properties of alkanes
1. Solubility
a) alkane is nonpolar
b) dissolve in nonpolar organic solvent e.g.: benzene, ether.
c) is hydrophobic and does not dissolve in water.
2. Boiling point
For straight chain alkane: b.pt increases as the molecular weight increase. Why?
3. Melting point
Increases as molecular weight increases.
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Physical properties of alkanes
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Alkane reactions
• Alkanes are the least reactive of all organic compounds. They do not usually react
with strong acids or bases, or with most oxidizing or reducing agents.
• They do, however, burn very easily in combustion reactions, releasing a great deal of
energy:
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Alkane reactions
• In the absence of enough oxygen for complete conversion to carbon dioxide, some
common waste products are generated in the incomplete burning of alkanes:
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Synthesis of alkanes
1) Hydrogenation of alkenes
CH3 CH3
+
CH3 C CH2 Ni CH3 C CH2
H2
H
+
H2 Ni
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2) Reduction of alkyl halide
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3) Hydrolysis of Grignard Reagent (Victor Grignard, Russian, Nobel Prize winner 1912)
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Alkane Sources; Petroleum Refining
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Fall 2020‐2021
Chapter 4: Alkenes
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Formulae for Alkene
• Alkenes are family of hydrocarbons containing at least one carbon‐
carbon double bond.
• Alkenes are unsaturated hydrocarbons with the presents of double

bond ( ═ )
Physical Properties
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Geometric (cis‐trans) Isomerism
The carbon‐carbon double bond doesn't allow any rotation about it. That
means that it is possible to have the CH3 groups on either end of the
molecule locked either on one side of the molecule or opposite each
other. These are called cis‐but‐2‐ene (where the groups are on the same
side) or trans‐but‐2‐ene (where they are on opposite sides).
Geometric (cis‐trans) Isomerism
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Physical Properties
When the number of carbon atoms increases:
• The physical properties increase

• The molecules get bigger and the molecular mass increase. So then,
the densities of the alkanes increase
• The molecules get bigger and the intermolecular force of attraction
becomes stronger. More energy is needed to overcome the strong
forces of attraction.
• The melting and boiling point increase.
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Chemical Properties
Chemical Properties
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Chemical Properties
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Markovnikov’s Rule
The major product is the one formed when the hydrogen adds to the carbon of the double bond that
already had more hydrogens prior to the reaction.
We say that such reactions are regiospecific when only one of two possible orientations of addition
occurs.
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In the addition of HX to an alkene, the H attaches to the carbon with fewer alkyl substituents and the X
attaches to the carbon with more alkyl substituents.
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Check your learning
What product would you expect from reaction of HCl with 1‐ethylcyclopentene?
Strategy
When solving a problem that asks you to predict a reaction product, begin by looking at the
functional group(s) in the reactants and deciding what kind of reaction is likely to occur. In the
present instance, the reactant is an alkene that will probably undergo an addition reaction with HCl.
Next, recall what you know about addition reactions and use your knowledge to predict the product.
You know that addition reactions follow Markovnikov’s rule, so H+ will add to the double‐bond carbon
that has one alkyl group (C2 on the ring) and the Cl will add to the double‐bond carbon that has two
alkyl groups (C1 on the ring).
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Check your learning
What product would you expect from reaction of HCl with 1‐ethylcyclopentene?
Solution
The expected product is 1‐chloro‐1‐ethylcyclopentane.
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Alkene Synthesis by High‐Temperature Industrial Methods
Catalytic Cracking of Alkanes
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Alkene Synthesis by High‐Temperature Industrial Methods
Dehydrogenation of Alkanes
Dehydrogenation is the removal of from a molecule, just the reverse of hydrogenation.

Dehydrogenation of an alkane gives an alkene.
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Naming Practice!!!
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
choose the correct ending

ene
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CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
determine the longest carbon chain with

the double bond
ene
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CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
assign numbers to each carbon

ene
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CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
assign numbers to each carbon

ene
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CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
attach prefix (according to # of carbons)

1-hexene
ene
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CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
determine name for side chains
1-hexene
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CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
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CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
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CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene
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Fall 2020‐2021
Chapter 5: Alkynes
Formulae
• Alkynes contain a triple bond.
• General formula is CnH2n‐2.
• Some reactions are like alkenes: addition and oxidation.
• Some reactions are specific to alkynes.
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Nomenclature: IUPAC
• Find the longest chain containing the triple bond.
• Change ‐ane ending to ‐yne.
• Number the chain, starting at the end closest to the triple bond.
• Give branches or other substituents a number to locate their position.
Nomenclature: IUPAC
CH3 C CH
propyne
CH3 C C CH2 CH2 Br
5-bromo-2-pentyne
5-bromopent-2-yne
CH3 CH3
CH3 CH CH2 C C CH CH3
2,6-dimethyl-3-heptyne
2,6-dimethylpept-3-yne
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Additional Functional Groups
All other functional groups, except ethers and halides have
a higher priority than alkynes.
Examples
OH
CH3 C C CH2 CH CH3
4-hexyn-2-ol
hex-4-yn-2-ol
Physical Properties
• Nonpolar, insoluble in water.
• Soluble in most organic solvents.
• Boiling points similar to alkane of same size.
• Less dense than water.
• Up to 4 carbons, gas at room temperature.
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Physical Properties
Acetylene
• Acetylene is used in welding torches.

• Approximately 20% of acetylene is supplied by the industrial
gases industry for oxyacetylene gas welding and cutting due to
the high temperature of the flame.
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Synthesis of Acetylene
• Heat coke with lime in an electric furnace to form calcium carbide.
• Then drip water on the calcium carbide.
Synthesis of Acetylene
The synthesis of acetylene from natural gas is a simple process.

Natural gas consists mostly of methane, which forms acetylene when
it is heated for a very short period of time.
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Synthesis by Elimination
Reagents for Elimination
Br Br
KOH (fused)
CH3 CH CH CH2 CH3 CH3 C C CH2 CH3
200°C
• KOH at 200C favors an internal alkyne.

• Sodium amide, NaNH2, at 150C, followed by water, favors a
terminal alkyne.
1) NaNH2 , 150°C
CH3 CH2 CH2 CHCl2 CH3 CH2 C CH
2) H2O
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Addition Reactions
• Similar to addition to alkenes.

• Pi bond becomes two sigma bonds.
• Usually, exothermic.
• One or two molecules may add.
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Addition of Hydrogen
Three reactions:
• Add lots of H2 with metal catalyst (Pd, Pt, or Ni) to reduce
alkyne to alkane, completely saturated.
• Use a special catalyst, Lindlar’s catalyst, to convert an alkyne
to a cis‐alkene.
• React the alkyne with sodium in liquid ammonia to form a
trans‐alkene.
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Lindlar’s Catalyst
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Addition of Halogens
• Cl2 and Br2 add to alkynes to form vinyl dihalides.

• So product is mixture of cis and trans isomers.
Br2 CH3 Br CH3 CH3

CH3 C C CH3 C C + C C
Br CH3 Br Br
Br2
Br Br
CH3 C C CH3
Br Br
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Addition of HX
• HCl, HBr, and HI add to alkynes to form vinyl halides.
• If two moles of HX is added, product is a dihalide.
Br Br
HBr HBr
CH3 C C H CH3 C CH2 CH3 C CH3
Br
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Hydroboration ‐ Oxidation
• BH3 (borane) adds to alkynes to give a vinylic borane

• Oxidation with H2O2 produces an enol that converts to the ketone or
aldehyde.
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Mercury(II)‐Catalyzed Hydration of Alkynes
• Mercuric ion (as the sulfate) is a Lewis acid catalyst that promotes addition
of water.
• The immediate product is a vinylic alcohol, or enol, which spontaneously
transforms to a ketone.
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Oxidation of Alkynes
• Similar to oxidation of alkenes.
• Dilute, neutral solution of KMnO4 oxidizes alkynes to a
diketone.
• Warm, basic KMnO4 cleaves the triple bond.
• Ozonolysis, followed by hydrolysis, cleaves the triple bond.
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Reaction with KMnO4
Mild conditions, dilute, neutral
O O
KMnO4
CH3 C C CH2 CH3 CH3 C C CH2 CH3
H2O, neutral
Harsher conditions, warm, basic
O O
KMnO4 , KOH
CH3 C C CH2 CH3 CH3 C O + O C CH2 CH3
H2O, warm
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Ozonolysis
Ozonolysis of alkynes cleaves the triple bond and gives two carboxylic
acids.
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Fall 2020‐2021
Chapter 6: Alcohols
ALCOHOLS
 Alcohols: Organic compounds containing
hydroxyl (‐OH) functional groups.
R OH
 Phenols: Compounds with hydroxyl group bonded

directly to an aromatic (benzene) ring.
OH
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Classification
carbinol
carbon
H CH3
atom
i) Primary (1 ) R C OH CH3CH2-OH CH3CHCH2 OH
H ethanol 2-methyl-1-propanol
ii) Secondary (2 ) R' OH

OH
R C OH H3C CH CH2CH3
H
2-butanol cyclohexanol
R' CH3
iii) Tertiary (3 )
R C OH H3C C OH
R '' CH3
2-methyl-2-propanol
Polyhydroxy Alcohols
 Alcohols that contain more than one OH group ‐

polyhydroxy alcohols.
 Monohydroxy: one OH group.
 Dihydroxy: two OH groups.
 Trihydroxy: three OH groups.
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Commonly encountered alcohols
 Methanol (CH3OH) finds use as a solvent in chemical reactions

and in fuel for high‐performance combustion engines.
 Methanol is metabolized to formaldehyde and formic acid by the

liver (alcohol dehydrogenase):
Formaldehyde Formic acid
alcohol
dehydrogenase
(oxidation) (oxidation)
 Ethanol (CH3CH2OH) is also metabolized by the body, and this reaction

produces acetaldehyde and acetic acid:
Acetaldehyde Acetic acid
alcohol
dehydrogenase
(oxidation) (oxidation)
 Excessive drinking leads to liver cirrhosis, physiological addiction, loss of

memory. Drinking during pregnancy poses risks for birth defects.
 Industrially, ethanol is synthesized by hydration of ethene.
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 Glycerol is a thick liquid that is normally present in the

body (it is a product of fat metabolism).
 Because of its affinity for water, it is often added to
pharmaceutical preparations such as skin lotions and soap,
and for shaving cream and glycerol suppositories.
Physical properties of alcohols
 Alcohols consist of: C H3 C H2 C H2 O H
 a non‐polar (alkane‐like) chain

alkane-like (non-polar) polar O-H bond
 a polar hydroxyl group
 Thus, alcohols might be water‐soluble, or not (depending on the length
of the carbon chain).
 We already saw that the boiling points of alkanes increase with increasing
chain length. The same is true for alcohols.
 Alcohols with more than one hydroxyl group (polyhydroxy alcohols) have
higher boiling points than monohydroxy alcohols.
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Preparation of alcohols
 Alcohols can be prepared by hydration of alkenes:
H2SO4
 They can also be prepared by the hydrogenation of C‐O double bonds:
H2
(Hydrogenation of this double bond is equivalent to a reduction in organic chemistry)
Chemical reactions of alcohols

Combustion reactions
 Any organic molecule can undergo a combustion reaction. In

combustion reactions involving alcohols, CO2 and H2O are
produced:
– CH3OH + O2  CO2 + 2H2O
– CH3CH2OH + O2  2CO2 + 3H2O
Or, for 2‐Propanol:
2 9 O2 6CO2 8H2O
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Elimination reactions
• In an intramolecular alcohol dehydration, a water molecule is

lost (eliminated) from a single alcohol molecule.
• The elimination involved loss of the OH group and a H‐atom
from an adjacent C‐atom (sometimes, there’s more than one of
these)
H2SO4
H-OH
180oC
H2SO4
H-OH
180oC
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 In general, these kinds of reactions (eliminations)

proceed as follows:
A-B
Two atoms (or groups of atoms) on neighboring carbons are removed,

leaving a multiple bond between these carbon atoms
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 Zaitsev’s Rule (for alcohol dehydrations): for cases where more

than one alkene product might be formed from an elimination
reaction, the hydrogen atom tends to be removed from the
carbon that already possesses the fewest hydrogens.
C H3 C H2 C H C H2
this carbon has this carbon has 1-butene
two H-atoms three H-atoms
H2SO4
C H3 C H2 C H CH3 + + H2O
180oC
OH
CH3 C H CH C H3
2-butene
major product
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Condensation reactions
 A condensation reaction is a reaction in which two molecules

(like two alcohol molecules) combine to form a larger molecule
while liberating a small molecule like water.
H2SO4
H2O
140oC
H2O
Dimethyl ether
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Oxidation reactions
Oxidation/reduction reactions involving organic compounds result in a

change in the number of H‐atoms and/or the number of O‐atoms bound
to carbons in the molecule:
Methanol Formaldehyde Formic acid
oxidation oxidation
reduction reduction
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Oxidation reactions
Primary and secondary alcohols can be oxidized by mild oxidizing
agents to produce compounds with C‐O double bonds
(aldehydes, ketones, carboxylic acids).
[O] [O]
an aldehyde a carboxylic acid
a primary alcohol
[O]
mild oxidizing
agent = [O]
a ketone
a secondary alcohol
[O]
no reaction
a tertiary alcohol 16
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Nomenclature of alcohols
This is the longest continuous chain that contains a

hydroxyl group.
Select this chain as the parent compound.
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4
3
2 1
This end of the chain is closest to the

OH. Begin numbering here.
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4
3
2 1
IUPAC name: 3-methyl-2-butanol

New IUPAC name: 3-methylbutan-2-ol
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This is the longest continuous chain that contains a

hydroxyl group.
Select this chain as the parent compound.
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5 4 3
2 1
This end of the chain is closest to the OH. Begin

numbering here.
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5 4 3
2 1
IUPAC name: 3‐methyl‐2‐pentanol
New IUPAC name: 3‐methylpentan‐2‐ol
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Nomenclature of cyclic alcohols
 Using the prefix cyclo‐

 The hydroxyl group is assumed to be on C1.
trans-2-bromocyclohexan-1-ol
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Nomenclature of alcohols containing two different functional

groups
1) Longest carbon chain that contains –OH group

‐ 5 carbon
2) Position of –OH group

‐ Carbon‐2
3) Position of C=C
‐ Carbon‐4
Complete name = 4‐penten‐2‐ol
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Nomenclature of alcohols containing two different functional groups
Some consideration:
‐ OH functional group is named as a hydroxy
substituent when it appears on a structure with a
higher priority functional group such as acids, esters,
aldehydes and ketones.
‐ Examples:
OH O OH
4 3 2
4 3 2 1 5 1
CH3 CH CH2 C OH 6
O
3‐hydroxybutanoic acid 2‐hydroxycyclohexanone
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Nomenclature of alcohols containing two different functional groups
MAIN GROUPS
Acids
Esters
Aldehydes
Ketones
Alcohols
decreasing priority Amines
Alkenes
Alkynes
Alkanes
Ethers
Halides
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Nomenclature of diols
 Alcohols with two –OH groups diols
 Naming of diols is like other alcohols except that the suffix

diol is used, and two numbers are needed to tell where the
two hydroxyl groups are located.
5
OH OH
4 1
3 2 1
CH CH CH 2 OH OH
3 3 2
IUPAC name propane-1,2-diol trans-cyclopentane-1,2-diol
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Nomenclature of phenols
 The terms ortho (1,2‐disubstituted), meta (1,3‐

disubstituted) and para (1,4‐disubstituted) are often used
in the common names.
OH
OH O2N OH
CH3CH2
Br
IUPAC name: 2-bromophenol 3-nitrophenol 4-ethylphenol
common name: ortho-bromophenol meta-nitrophenol para-ethylphenol
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Nomenclature of phenols
 Phenols may be monohydric, dihydric or trihydric ‐

(number of hydroxyl groups) in the benzene ring.
OH
OH OH
OH
OH OH
OH
benzene-1,3-diol benzene-1,4-diol benzene-1,2,3-triol
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Thank you for attention
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Fall 2020‐2021
Chapter 7: Carboxylic acids
Introduction
The functional group of carboxylic acids consists of a C=O
with ‐OH bonded to the same carbon.
Carboxyl group is usually written ‐COOH.
Aliphatic acids have an alkyl group bonded to ‐COOH.
Aromatic acids have an aryl group.
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IUPAC Names
Remove ‐e from alkane (or alkene) name, add ‐oic acid.

The carbon of the carboxyl group is #1.
Ph H
Cl O C C
CH3CH2CHC OH H COOH
2‐chlorobutanoic acid trans‐3‐phenyl‐2‐propenoic acid
(cinnamic acid)
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Physical Properties: Boiling Points
 Higher boiling points than similar alcohols, due to dimer

formation.
 A chemical entity consisting of two structurally similar monomers
joined by bonds.
Acetic acid, b.p. 118C
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Physical Properties:
Melting Points
 Aliphatic acids with more than 8 carbons are solids at

room temperature.
 Double bonds (especially cis) lower the melting point.
 Note these 18‐C acids:
 Stearic acid (saturated): 72C
 Oleic acid (one cis double bond): 16C
 Linoleic acid (two cis double bonds): ‐5C
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Acidity
 A carboxylic acid may dissociate

in water to give a proton and a
carboxylate ion.
 The equilibrium constant Ka for
this reaction is called the acid‐
dissociation constant.
 The pKa of an acid is the negative
logarithm of Ka, and we
commonly use pKa as an
indication of the relative acidities
of acids.
4
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Salts of Carboxylic Acids
Sodium hydroxide removes a proton to form the salt.
Adding a strong acid, like HCl, regenerates the carboxylic acid.
10
10
5
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Saponification
 “Soap‐making”
 Base‐catalyzed hydrolysis of ester linkages in fats and oils.
O CH2 OH
CH2 O C (CH2)16CH3 CH OH
O
CH2 OH
CH O C (CH2)16CH3 + 3 NaOH
O O
+-
CH2 O C (CH2)16CH3 + 3 Na O C (CH2)16CH3
Soap
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11
Synthesis Review
Oxidation of primary alcohols and aldehydes with
chromic acid.
Cleavage of an alkene with hot KMnO4 produces a
carboxylic acid if there is a hydrogen on the double‐
bonded carbon.
Alkyl benzene oxidized to benzoic acid by hot KMnO4 or
hot chromic acid.
12
12
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Synthesis
Oxidation of primary alcohols and aldehydes with
chromic acid.
13
13
Synthesis
Cleavage of an alkene with hot KMnO4 produces a
carboxylic acid if there is a hydrogen on the double‐
bonded carbon.
14
14
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Synthesis
Alkyl benzene oxidized to benzoic acid by hot KMnO4 or

hot chromic acid.
15
15
Some Important Acids
Acetic acid is in vinegar and other foods, used industrially
as solvent, catalyst, and reagent for synthesis.
Fatty acids from fats and oils.
Benzoic acid in drugs, preservatives.
Adipic acid used to make nylon 66.
Phthalic acid used to make polyesters.
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CHEM331 Organic Chemistry (3 CR.) : Fall 2020 2021

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11/19/2020

ORGANIC CHEMISTRY FUNCTIONAL GROUPS

ALKYL HALIDE ALCOHOLS & PHENOLS

ALIPHATIC CYCLIC AROMATIC

RULE 1: THE MAIN CHAIN

RULE 1: THE MAIN CHAIN

RULE 2: NUMBERING THE MAIN CHAIN

RULE 3: NAMING ALKYL GROUPS Name the substituent groups.

RULE 3: NAMING ALKYL GROUPS Name the substituent groups.

RULE 3: NAMING ALKYL GROUPS Name the substituent groups.

RULE 3: NAMING ALKYL GROUPS Name the substituent groups.

RULE 3: NAMING ALKYL GROUPS Name the substituent groups.

RULE 4: ORGANIZING MULTIPLE GROUPS

RULE 4: ORGANIZING MULTIPLE GROUPS

RULE 4: ORGANIZING MULTIPLE GROUPS

• Alkenes are unsaturated hydrocarbons with the presents of double

When the number of carbon atoms increases:

• The physical properties increase

Dehydrogenation is the removal of from a molecule, just the reverse of hydrogenation.

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

choose the correct ending

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

determine the longest carbon chain with

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

assign numbers to each carbon

CH2 CH2 CH3

assign numbers to each carbon

CH2 CH2 CH3

attach prefix (according to # of carbons)

CH2 CH2 CH3

CH2 CH2 CH3

CH2 CH2 CH3

CH2 CH2 CH3

• Acetylene is used in welding torches.

The synthesis of acetylene from natural gas is a simple process.

• KOH at 200C favors an internal alkyne.

• Similar to addition to alkenes.

• Cl2 and Br2 add to alkynes to form vinyl dihalides.

Br2 CH3 Br CH3 CH3

• BH3 (borane) adds to alkynes to give a vinylic borane

 Phenols: Compounds with hydroxyl group bonded

ii) Secondary (2 ) R' OH

 Alcohols that contain more than one OH group ‐

Commonly encountered alcohols

 Methanol (CH3OH) finds use as a solvent in chemical reactions

 Methanol is metabolized to formaldehyde and formic acid by the

Formaldehyde Formic acid

Commonly encountered alcohols

 Ethanol (CH3CH2OH) is also metabolized by the body, and this reaction

 Excessive drinking leads to liver cirrhosis, physiological addiction, loss of

Commonly encountered alcohols

 Glycerol is a thick liquid that is normally present in the

Physical properties of alcohols

 Alcohols consist of: C H3 C H2 C H2 O H

 a non‐polar (alkane‐like) chain

Chemical reactions of alcohols

 Any organic molecule can undergo a combustion reaction. In

Or, for 2‐Propanol:

Chemical reactions of alcohols

• In an intramolecular alcohol dehydration, a water molecule is