SRC - Organic Chemistry PDF

ORGANIC CHEMISTRY
Organic Chemistry
Organic Chemistry
- the study of organic compounds and their reactions,
properties, naming, structures and equations
Organic Compounds?
- Contain the element Carbon (C) and are held covalently.
Ex. of C containing compound w/c are not ORGANIC

1. CaCO3- chalk
2. NaHCO3 – baidking soda, ant
3. NaCN – toxic salt
Organic Chemistry MCL2018 2

Polarity of Organic Compounds
• Organic compounds – could either be polar or a nonpolar.
• If bond – based on ΔEN

• If whole molecule – dipole moment
sugar Hexane (gasoline)

Properties of Organic Compounds
1. Composition
- composed of few elements like C, H, O ,N, P, S, X
(Halogens)
- usually a bonding between non-metal elements.
2. Bonding
- Through covalent bonding
- Ionic compounds- for inorganic
3. Solubility
- If polar, soluble in H2O
- If nonpolar, then insoluble in H2O

Properties of Organic Compounds
4. Melting Point(MP) and Boiling Pt(BP)
- Organic cpds - have lower BP/MP
- Inorganic cpds – Higher BP/MP
Reason: Intermolecular force of attraction(IMFA)
5. Isomerism
- displayed by organic compounds
- a phenomenon where 2 or more compounds have the
same MF(Molecular Formula) but different in structures.

Structures of organic compounds
1. Molecular Formula
2. Condensed Formula
3. Expanded Structure
4. Lewis Structure
Example: Pentane
- (-ane : indicates that all bonds are single ( )
Gen formula: CnH2n+2
n= no. of Carbon
How many isomers?

MF: C5H12

Covalent bond
- Sharing of e- bet 2 or more nonmetals
General:
• C - 4 covalent bonds & 0 unshared electron pair
• O – 2 covalent bonds & 2 Unshared electron pairs
• N – 3 covalent bonds & 1 unshared electron pair
• H – 1covalent bond & 0 electron pair
• ( F, Br, I & Cl) - 1 covalent Bond & 3 unshared electron pair
• Exercise in Lewis structure:

Covalent Bonds
.. .. ..
•Single bond: H H H Br
.. : : Br
..
Br
..
:
:O O..:
•Double bond: ..
N N
•Triple bond: .. ..

Covalent Bonds
Classification:
1. Whether e- sharing is equal or not
a. If the sharing is equal, the molecule is Nonpolar
b. If the sharing is unequal, the molecule is Polar
Why UNEQUAL?
- Because atoms have different ElectroNegativity (EN)

Classification of Covalent Bonds
2. Manner of Overlapping
a. Sigma Bond (σ)
-End to end or head on overlapping of orbitals
- strong bond
- overlap is more effective
- it is the first to be formed in a molecule.
. + . : :
S orbital S orbital
H H H. .H H H

Classification of Covalent Bonds
b) Pi bond or  bond
-Happens when the overlap is lateral or sideways
- Py and Pz orbitals
. . . .
+
. . . .
Pz orbital Pz orbital
. . . .
+
. . . .
Py orbital Py orbital

Atomic Orbitals
1. Pure Orbitals
Ex. S :
P:
Px Py Pz
2. Hybrid Orbitals
- Combination of Atomic Orbitals
-Stronger than AO
-No. of AO = No. of HO
Classes of Hybrid Orbitals
a. sp
b. sp2
c. sp3
Hybridization of Nitrogen
• Elements other than C can

have hybridized orbitals
• H–N–H bond angle in
ammonia (NH ) 107.3°
• N’s orbitals (sppp) hybridize to
3
3
form four sp orbitals
• One sp orbital is occupied by
3
two nonbonding electrons, and

three sp3 orbitals have one
electron each, forming bonds
to H

Hybridization of Oxygen in Water
• The oxygen atom is sp -hybridized

3
• Oxygen has six valence-shell electrons but forms

only two covalent bonds, leaving two lone pairs
• The H–O–H bond angle is 104.5°

Properties of Covalent Bonds
1. Bond Polarity
2. Bond Energy
3. Bond Length
4. Bond Angle
5. Bond Order

Bond Polarity
Bond polarity (BP)- due to differences in electronegativity
- the more unequal the sharing of e-, the stronger the

attraction bet 2 atoms, the higher is the BP.
Factors affecting bond polarity

1. Difference in EN
2. Formal charge
3. Nature of surrounding atoms
4. Type of hybridization

Bond Polarity
•1. Difference in the Electronegativity (ΔEN)
So, ΔEN : BP ( the more the unequal is the sharing)
H= 2.1 C=2.5 N=3 O=3.5 F=4.0

Which bond is the most polar?_____ The least polar?_____
a) H-F
b) H-O
c)H-N
d)H-H

Bond Polarity
2. Formal charge (FC)
FCA = (Group No. of A) - ½(bonding e-) - (e- in the LP)
FC = + (gives away e-, e- poor), polarity enhanced

FC = - (takes e-, e- rich), polarity enhanced
FC = 0 (not affected by its neighboring atoms)

Bond Polarity
1. Which N-H bond is more polar?

a) NH3 or b) NH4
2. Which OH is more polar?

a) H3O+ or b) H2O
FC=O
FC = +1 bond is more polar, central atom is electron poor

Bond Polarity
3. Nature of the Surrounding Atoms
Which is more polar?

Which is the less polar?
a) CCl3H or b)CH3Cl?
Note: the more EN the atoms are around the C, the

poorer the C is to the EN atom, therefore, the more polar
is the bond

Bond Polarity
4. Type of Hybridization
s character (%S) = EN, BP
hybrid %s %p
sp3 ¼= 25% ¾= 75%
sp2 1/3=33.33% 2/3= 66.7%
sp ½= 50% ½= 50%
Which bond is the most polar?
H3C CH2 H HC C H H2C CH H
•Note: higher s character = more EN, therefore the more

polar the bond is.

Bond Energy (BE), Bond Strength
• The energy needed to break a bond
-The stronger the bond, the higher the BE, the more polar
the bond
-Ξ>=>-
• BP: BE
Which is has higher Bond Energy?

N H < O H
More polar

Bond length
• the distance between 2 bonded atoms that leads to a
maximum stability
Factors affecting bond length:

1. Size of the Atom – the larger the atomic radius, the
longer the bond length
2. Bond polarity – the more polar, the stronger the
attraction, the closer are the atoms, the shorter the bond
length.
3. Number of bonds – multiple bonds result to stronger
attraction, thus, shorter bond length
HC CH H2C CH2 H3C CH3

Bond Angle
• the angle between two adjacent bonds

FUNCTIONAL GROUPS

Saturated. Unsaturated. Derivatives
HYDROCARBONS

Introduction
Hydrocarbons – compounds that contain carbon and
hydrogen only

Saturated Hydrocarbons
- has only single bonds between C atoms
- belong to the alkane family.
Number of C Name MF
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

Unsaturated Hydrocarbons
• Unsaturated hydrocarbon
- has either a double (alkene (b)) or triple bond (alkyne
(c)) between two carbon atoms.
• Aromatic hydrocarbon has a benzene ring (d).

Alkanes
• Saturated HC
• end in the suffix -ane.
• Contain the maximum number of hydrogen atoms that
can bond with the number of carbon atoms in the
molecule.
• General molecular formula: C H n 2n+2.
Pentane has 5 carbon atoms and 12 (2 × 5 + 2 = 12)

hydrogen atoms, C5H12.

Learning Check
What is the molecular formula of alkane w/c contains
C11= undec-
1. 11 carbon atoms (undecane) C11H24
C12= dodec-
2. 12 carbon atoms (dodecane) C12H26 C13= tridec-
3. 13 carbon atoms(tridecane) C13H28 C14= tetradec-
4. 20 carbon atoms (icosane) C20H42 C15= pentadec-
5. 21 carbon atoms (henicosane)C21H44 C16= hexadec-
C17= heptadec-
C18= octadec-
C19= nonadec-
C20= eicos-

Classes of carbons
1. Primary Carbon (1°) – attached to 1 other carbon
(Terminal C)
2. Secondary C (2°) – attached to 2 other C’s (Branch)
3. Tertiary C (3°) – attached to 3 other C’s (middle)
Example: 3-methylpentane
How many are?
1. 1° C= 1. 1° H =
2. 2° C = 2. 2° H =
3. 3 °C = 3. 3° H =

ALKYL GROUPS (R -)
- Appears as branch(es)
When a hydrogen is removed from an alkane, an alkyl
group results.
CH3 – H = CH3–
methyl group
methane
CH3-CH2 – H = CH3-CH2–
ethane ethyl group
The suffix name (ane) is changed to -yl.

Alkyl Groups

Nomenclature of Alkanes
1. Select the longest chain as the parent chain
H3C CH CH 2 CH CH3
H2 C CH3 CH3
2. Number the chain from the end nearer to the first branch
3. Multiple, identical branches use di (2), tri (3), tetra (4) to

denote no. of C but do not include the di, tri, tetra in
alphabetizing.
(Note: cyclo and iso prefixes are included in alphabetizing)
4. Name the branches in alphabetical order, separate

number by a , (comma); separate number from text by a –
(hyphen)
5. Each branch gets a locating no.
CH3
H3C CH2 CH CH CH CH3
H2 C CH3 CH3
6. When 2 different groups compete for the same position,

give lower number to the group ahead in the alphabet
H3C H2C CH3
H3C CH 2 CH CH 2 CH CH CH 2 CH3

7. When 2 chains are equal in length, select chain with
1
more branches H C CH 2 3
H3C CH 2 CH CH 2 CH CH3
HC CH3 2
How many branches:____
CH3 Heptane
Parent:_________
H2 C CH3
H3C CH 2 CH CH 2 CH CH3
HC CH3 3
How many branches:____
CH3
Heptane
Parent:_________
1
PREFIX – PARENT – LOCANT - SUFFIX

Learning Check
What is the name of the following examples?
1.
2.

Learning check
3.
CH3 CH3
CH3 CH CH CH2 CH2 CH3
CH3
4. CH3 CH C CH2 CH2 CH3
CH3

5.
Br NO2
CH3 CH CH CH3
1 2 3 4
Br NO2
CH2 CH2 CH CH3

1 2 3 4

Learning check
The ff names are incorrect. Draw and give the correct name
1. 5-bromo-3-chlorohexane
2. 2 ethyl-5-isopropylhexane

Cycloalkanes
Cycloalkanes- alkanes whose carbon atoms are joined in
rings
General formula CnH2n where n = 3,4,…
• Prefix: Cyclo
• Suffix: -ane
• Name: Cyclo-rootword-ane
CH 2
• or
H2C CH 2
cyclobutane cyclopentane cyclohexane
cyclopropane

Nomenclature of Cycloalkane w/ 1 Branch (-R)
Name:
1. Name the –R group
2. Name the cycloalkane
Note:
• Parent- is the cycloalkane
Isopropylcyclohexane
• No need to locate for the branch
• No need.
to number as well
ethylcyclopentane methylcyclobutane t-butylcyclopentane

Nomenclature of Cycloalkane
• But if –R is very long and COMPLEX (no name for –R),
then the ring will be a branch
CH3 CH3 CH3
H3C CH C CH CH 2 CH3
3-cyclopentyl-2,3,4-trimethylhexane

Nomenclature of Cycloalkane
• When the ring or cycloalkane becomes a branch
- Ending: -yl
- Name: cycloalkane  cycloalkyl
cyclopropane  cyclopropyl
Ex:
cyclopropyl cyclobutyl cyclopentyl cyclohexyl
• Note: cyclo prefix is considered when alphabetizing.

Learning Check
1.
CH 2 CH 2 CH 2 CH 2
1,4-dicyclohexylbutane
2. I
H3 C CH CH CH CH 2 Br
CH
H3C CH3
1-bromo-2-cyclopropyl-4-iodo-3-isopropylpentane

Learning check
1. CH 2 CH3 2. CH 2 CH3
CH3
3. H3C 4. H3C CH2 CH3

H3C
H3C

Nomenclature of Alkenes & Alkynes
ALKENES ALKYNES
Gen. Formula CnH2n CnH2n -2
Smallest # C2H4 C2H2

H H
C C
H C C H
H H
Suffix -ene -yne

IUPAC: Ethene IUPAC: Ethyne
CN: Ethylene CN: Acetylene

Alkenes Alkynes
H3C CH CH2 H3C C CH
1 1
• Note: notice that the double and triple bond are in C1 & C2
H3C CH2 CH CH2 H3C C C CH3
But-1-ene But-2-yne
H3C CH CH CH3 HC C CH2 CH3
But-2-ene
But-1-yne
Positional Isomers
What kind of isomers are they? _____________

1. Select the parent Chain: the longest continuous chain that
passes through double bond or triple bond.
1 5
H2C C CH2 CH2 CH3
H2C CH3
Name: 2-ethylpent-1-ene
2. No the parent chain from the end nearer the = or Ξ bond
3. Name the branches, name the parent

4. If from either end, the location of the = or Ξ is the same;
consider the branches. Start from the end nearer to the
branch.
H3C CH CH C CH2 CH3
CH3 H2C CH3
Name: 4-ethyl-2-methylhex-3-ene
5. Choose the branch ahead in the alphabet

CH3
H3C CH 2 C C CH 2 CH3
H2C CH3

Suffix
• One = bond; -ene
• One Ξ bond; -yne
• Two = bonds; -diene
• Two Ξ bonds; -diyne
To name: from ALKANE  ALKADIENE

ALKANE  ALKADIYNE
H2C CH CH CH2 HC C CH2 C CH
Name: Buta-1,3-diene Name: penta-1,4-diyne

Nomenclature of Cycloalkenes
- A cyclic compound with a double bond
cyclopropene cyclobutene cyclohexene

cyclopentene
Note: if unsubstituted, no need to no. the ring (= is always
bet C1 & C2)
For monosubstituted Cycloalkene
1. Ring is the parent cycloalkene
2. Numbers 1 and 2 always go to the = bond
3. Rest of the ring is numbered to give lowest possible no. to
the branches 3
Name: 3-methylcyclopropene
1 2
4. No need to locate for the double bond
5. #-name of the branch, name of the parent
Cycloalkadiene
Cyclobuta-1,3-diene cyclobutadiene
Cyclopenta-1,3-diene cyclopentadiene
Cyclohexa-1,3-diene
Cyclohexa-1,4-diene

Learning Check
H3C CH 2
CH 2 CH3 CH3
CH 2

Learning Check

Index of Hydrogen Deficiency
- Refers to the Degree of Unsaturation (DU)
General Rules:
1. With the presence of multiple bonds or cyclic chains:
DU= (max. # of H- actual # of H) / 2
2. With the presence of oxygen:
Ignore the number of O and proceed with Rule # 1.
3. With the presence of nitrogen:
For every N, remove one H and proceed with Rule # 1.
4. With the presence of halogen:
For every X, add one H and proceed with Rule # 1.

Aromatic Hydrocarbons
-How many  e- pairs: 3

- hybridization: sp2
- it displayed resonance
NAMING:
1. Monosubstituted Benzene
2. Disubstituted Benzene
3. Polysubstituted

Nomenclature of Aromatic Hydrocarbons
1. Monosubstituted Benzene
-NAME: substituent + Benzene (PARENT)
H3C CH3 CH3

Recall Br NO 2
H3C C
-NO2 - nitro
CH3
-CN - cyano
-NH2 - amino
Isopropyl bromo t-butyl nitro
- F - fluoro benzene benzene benzene benzene
-Cl - chloro
-Br - bromo

Common names of some monosubstituted benzene:
- Accepted as IUPAC name CH=CH 2
OH COOH
phenol
CH3
Benzoic acid styrene
SO3H
toluene NH2
CHO aniline Benzene

Benzaldehyde sulfonic acid

2. Disubstituted Benzene
X X X
X X
(1,2)- ortho (1,3)- meta (1,4)- para
-Positional isomers
- use as common names

Cl
•.
H3C CH3
CH3
IN: 1,4-dimethylbenzene CH3

IN: 1-chloro-3-isopropylbenzene
CN: p- dimethylbenzene CN: m-chloroisopropylbenzene
I OH
CN
NO 2
IN: 1-cyano-2-iodobenzene IN: 4-nitrophenol
CN: o-cyanoiodobenzene CN: p-nitrophenol

CH 3 H3C CH3
Br
NH2
IN: 2-bromotoluene
IN: 4-isopropylaniline
CN: o-bromotoluene
CN: p-isopropylaniline
Note: O,M,P can only be used if it is disubstituted

3. Polysubstituted
H3C CH3
IN: 1,2,4,5-tetramethylbenzene
H3C CH3
NO 2
1 CH3
IN:2,4,6-trinitrotoluene
O 2N 2 NO 2

Learning Check
CH=CH 2
SO3H
1. 4.
H3CH 2C CH 2CH 3
I
CHO
CN
2. 5.
CH3
H3CH 2C CH 2CH 3
I Cl
COOH
3.
H3C NO 2

•BENZENE ring can also be a BRANCH.
. phenyl
CH 2----- benzyl

Learning Check
1.
CH2 CH2 CH2 CH2------- 1,4-diphenylbutane
2. CH 2 CH CH2 3-phenylpropene
3. C C CH2 CH CH3 4-methy-1-phenylpent-1-yne

CH3
4. 1,2-diphenylcyclohexane

Learning Check
5.
6 5 3-benzyl-6-phenylcyclohexene
1 4
2 3
CH 2

Oxygen Derivatives
1. Alcohols and ethers
ALCOHOLS
CN: Name of the alkyl groups or cycloalkyl group + suffix
alcohol
CN
CH3-OH Methyl alcohol
CH3CH2-OH Ethyl alcohol
CH3CH2CH2-OH Propyl alcohol
H3C CH3
CH Isopropyl alcohol
OH

Nomenclature of Alcohols
CH3CH2CH2CH2-OH butyl alcohol
ISOMERS
H3C CH2 CH2 CH3 S-butyl alcohol
OH
H3C CH CH2 OH
isobutyl alcohol
CH3
CH3
H3C C OH T-butyl alcohol

CH3

CN
OH
cyclopropyl alcohol
cyclobutyl alcohol
OH
OH
cyclopentyl alcohol
OH cyclohexyl alcohol

1. Parent Chain: Find the longest chain containing the C-OH
2. Name of the parent: name of the alkane , then change the
ending e to –ol
Ex. Alkane  Alkanol
methane methanol
ethane ethanol
propane propanol
butane butanol
pentane pentanol
* Ending OL- denotes the presence of ALCOHOL

If there are two –OH,
IN: alkane-#,#-diol (If aliphatic)
cycloalkane-#,#-diol (If cyclic)
OH
H2C CH 2
Cyclohexane-1,2-diol
OH OH
OH
Ethane-1,2-diol OH
H3C CH CH2
Cyclohexane-1,4-diol
OH OH
OH
Propane-1,2-diol

• If both =/ bond and –OH are present, give priority to the
ALCOHOL
• Suffix: Root-#-en-#-ol (double bond)
Root-#-yn-#-ol (triple bond)
OH
H2C CH CH CH3
1. 3.
OH
but-3-en-2-ol cyclohex-2-enol
2. H3C C C CH2 CH2 OH
pent-3-yn-1-ol

Nomenclature of Ethers
Ether- (R-O-R)
CN: Name of the two R-groups + suffix Ether
CN IN
CH3-O-CH3 dimethyl ether Methoxy methane
CH3CH2-O-CH3ethyl methyl ether Methoxy ethane
CH3CH2-O-CH2CHdiethyl
3.
ether Ethoxy ethane
H3C O cyclopentyl methyl Methoxy cyclohexane

ether

• O CN IN
Dicyclohexyl ether cyclohexoxy cyclohexane
O
Diphenyl ether Phenoxy benzene
Cyclohexyl phenyl ether Phenoxy

cyclohexane

R Parent Alkane
OR Alkoxy branch
RO- alkoxy (Alkyl into oxy)
CH3O- methoxy
CH3CH2O- ethoxy
CH3CH2CH2O- propoxy
O-- phenoxy

OCH 3
H3C CH2 CH2 OCH3 IN:3-methoxyphenol
IN: 1- methoxypropane OH
CH3
H3C CH2 CH3

IN:3,5-dimethoxytoluene
OCH3
H3CO OCH 3
IN: 2-methoxypropane CH3
H3C CH2 CH2 CH CH3
OCH2CH3 O O
IN: 2-ethoxypentane
IN:3,5-diphenoxytoluene
•. HO
H3CH 2CO O
OCH 3
6-ethoxy-3-methoxy-2-phenoxycyclohexanol

ALDEHYDES & KETONES
O O
R C H R C R
R-CHO R-COR
•Now, w/c Carbon is more +?

O O
R C H R C R
σ+ σ+
More + bec only 1 e- Less + bec only 2 e-

releasing grp releasing grp

ALDEHYDES & KETONES
Smallest ALDEHYDE Smallest KETONE
O O
H C H H3C C CH3
- Formaldehyde -Dimethyl ketone or

(Formalin) (Acetone)
- Use as - Use as solvent
preservative or
embalming sol’n

Nomenclature of Aldehydes and Ketones
Common Names: RW+Aldehyde
Common Names IUPAC Name
1. H-CHO Formaldehyde methanal
2. CH3-CHO Acetaldehyde ethanal
3. CH3CH2-CHO Propionaldehyde propanal
4. CH3CH2CH2-CHO Butryaldehyde Butanal
5. CH3CH2CH2CH2-CHO Valeraldehyde Pentanal
IUPAC Name:
1
1. Count the # of carbon starting from the -CHO
2. Name the parent = as the name of the alkane with
ending e AL

OH
1. 6 5 3 2 1 Note: OH- hydroxy
H3C CH 2 CH CH CH 2 CHO
4
(Branch)
H2C CH3
3-ethyl-4-hydroxyhexanal
5 4 3 2 1
2. H3C CH CH CH2 CHO
pent-3-enal (No need to put 1 for CHO)
3. CHO
Benzaldehyde

CN: Name of the 2 R-groups + Ketone
CN IUPAC Name
1. CH3-CO-CH3 Dimethyl ketone Propanone
2. CH3CH2-CO-CH3. Ethyl methyl Ketone Butanone
3. CH3-CO-CH2CH2CH3 Methyl Propyl Ketone Pentan-2-one
4. CH3CH2-CO-CH2CH3. Diethyl ketone Pentan-3-one
IUPAC NAME:
1. Parent chain is the longest chain that passes through O
. C .
2. Name the parent= name of alkane w/ ending e change
into -one.
O
3. Start numbering at carbon nearer the . C .

Learning Check
H3C CH2 CH2 CH2 C CH3 hexan-2-one
H3C C CH CH CH3 pent-3-en-2-one

O
• If the molecule has both a . C . and –CHO, then the

priority will be the –CHO, always at # 1.
O
• . C . - is considered as a substituent and it is called

OXO.
O
H3C C CH 2 CH CH CHO
5-oxohex-2-enal

O O
H3C C CH 2 C CHO
2,4-dioxopentanal
O O
H3C C CH 2 C CH3
Pentane-2,4-dione

O O
H C CH 2 CH 2 C H
butanedial
-No need to locate because they are always on the two ends
-DIAL- means 2 aldehydes at the two ends.

( Applicable to Aldehyde but not to Ketone)

•IN: Cycloalkanone (no need to no. the C=O, always at # 1)
O
Cyclobutanone
O Cyclopentanone
OCH3
O Cyclohexanone
5-methoxycyclopent-2-enone

Learning Check
Matching type:
____1. propanone a. diethyl ketone

____2. 3-pentanone b. dimethyl Ketone
____3. Butyraldehyde c. Pentanal
____4. 2-pentanone d. Butanal
e. Methyl propyl ketone

CARBOXYLIC ACIDS
O
R C O H Or R-COOH
-COOH  this group is called carbonyl acid group

O
. C  carboxylate (all atoms are sp2 and are

O .
stabilized by resonance)

Nomenclature of Carboxylic Acids
CN: RW + -ic acid IN: RW + -oic Acid
H-COOH Formic Acid/ Methanoic Acid
ant’s bite
Acetic Acid/ Ethanoic Acid
CH3-COOH
Vinegar
Propanoic Acid
CH3CH2-COOH Propionic Acid
CH3CH2CH2-COOH Butyric Acid Butanoic Acid
Valeric Acid Pentanoic Acid

CH3CH2CH2CH2-COOH

O
H3C CH2 CH2 CH2 CH CH CH2 C OH
Oct-3-enoic acid
HOOC CH2 CH2 CH2 COOH
Pentanedioic acid
• No need to locate the two –COOH because they are

always on the 2 ends

OH O
H3C CH2 CH CH CH C COOH
OCH3
4-hydroxy-3-methoxy-2-oxohept-5-enoic acid
Cyclic Carboxylic Acid

* Cycloalkane + carboxylic Acid
COOH
Cyclobutane carboxylic acid
COOH
Cyclopentane carboxylic acid

•.
COOH Cyclohexane carboxylic acid
HOOC
4-hydroxycyclopent-2-ene carboxylic acid

HO

ACID DERIVATIVES
..
..
O
..
R C NH2
1. Acid Amide
O
..
..
..
2. Ester R C O R
..
O
3. Acid Halides ..
R C X
.. ..
..
..
O O
..
..
4. Anhydride ..
R C O C R
..

AMIDE: IUPAC NAMING
CN: RW + Amide IN: ALKANAMIDE
1. H-CO-NH2 FORMAMIDE METHANAMIDE
ACETAMIDE ETHANAMIDE
2. CH3-CO-NH2
3. CH3CH2-CO-NH2 PROPIONAMIDE PROPANAMIDE
BUTANAMIDE
4. CH3CH2CH2-CO-NH2 BUTYRAMIDE
VALERAMIDE PENTANAMIDE
5. CH3CH2CH2CH2-CO-NH2

AMIDE: IUPAC NAMING
• If Aromatic, O
NH2
BENZAMIDE
-just memorize
• If N has
O a substituent:
CN: N-ethylacetamide
H3C C N CH 2CH 3
IN: N-ethylethanamide
2 1 H
CN: N-ethyl-N-phenylbutyramide
H3CH 2CH 2C C N
CH 2CH 3 IN: N-ethyl-N-phenylbutanamide

AMIDE: IUPAC NAMING
•. O
H3CH 2CH 2C C N
CN: N,N-diphenylbutyramide
IN: N,N-diphenylbutanamide
C N
IN: N,N-diphenylbenzamide

ACID HALIDE: IUPAC NAMING
CN: RW + yl + name of the halide IN: Alkanoyl+ halide
O
1. H C Br CN: formyl bromide IN: methanoyl bromide

O
2. H3C C Cl
CN: acetyl chloride IN: ethanoyl chloride
O
3. H3CH2C C Br CN: propionyl bromide IN:propanoyl bromide

O
4. CN: butyryl bromide IN:butanoyl bromide

H3CH2CH2C C Br
O
5. H3CH2CH2CH2C C BrCN: Valerylbromide IN:pentanoyl bromide

ACID HALIDE: IUPAC NAMING
• If Aromatic, O
-benzoyl chloride
Cl

ACID ANHYDRIDE: IUPAC NAMING
-Are derived from two acids
O O
R C O R
1. Identify the two acids + anhydride

If in CN: RW+ic RW+ic anhydride
If in IN: alkan+oic alkan+oic anhydride (alphabetical)
O O CN: acetic formic anhydride
: 1) H C O C CH3 IN: ethanoic methanoic
anhydride
FORMIC ACETIC

ACID ANHYDRIDE: IUPAC NAMING
• If identical, then name it once.
O O
C O C Benzoic anhydride
O O
H3CH2CH2CH2C C O C CH2CH3
1 1
CN: propionic valeric anhydride
IN: pentanoic propanoic anhydride

ESTERS: IUPAC NAMING
-Is a combination of an acid and alcohol
O
Alcohol
R C O OR
Acid
•Name the R- group (like alkyl, phenyl, cycloalkyl) from

alcohol
- CN: Name the acid w/c ends in -ic acid into –ate
- IN: Name the acid w/c ends in –oic acid into-oate

O
CN: methyl formate
H C O CH3
IN: methyl methanoate
C O CH 2CH 3
ethyl benzoate
C O
phenyl benzoate

•. O
H3CH 2CH 2C C O
CN: phenyl butyrate
IN: phenyl butanoate

ISOMERISM

Isomerism
Isomers
Structural Isomers Stereoisomer
Chain Position Functional 1. Conformational

2. Geometric
Usually displayed by: displayed by the ff pair: Cis/Trans
displayed : 1. Alkenes 1. Alcohol & Ether 3. Optical Isomers
1. Alkanes 2. Alkynes 2. Ketone & aldehyde
2. Cyclo- 3. Alcohol 3. Carboxylic acid &
alkanes 4. Alkyl esters
halides
5. ketones

ISOMERS
Isomerism-Is a phenomenon where in 2 or more compounds
have the same MF but different in structures .
Kinds of Isomers:
1. Structural Isomers- different structure
2. Stereoisomers -same structure
- but different arrangement of atoms in
space

Structural Isomers: Chain Isomers
1. Chain Isomers-
- usually displayed by ALKANES & CYCLOALKANES.
- have same MF but different points of attachment
Give the isomers of

a. pentane
b. 3-methylpentane
c. cyclopentane

Structural Isomers: Position Isomers
2. POSITION ISOMERS
- Have the same chain/parent but different in position of the
functional group.
- Can be displayed by alkene, alkynes, alcohol, ketone,
alkyl halide.
•Give the positional isomers of the ff:

1. pent-2-ene
2. but-1-yne
3. hexan-2-ol
4. pentan-2-one
5. 1-chlorocyclohexene

Structural Isomers: Functional Isomers
3. FUNCTIONAL ISOMERISM
- Same MF but different in functional groups
- Functional isomerism should be in pairs or in partners.
It can be exhibited by:

a. Alcohol (R-OH) & Ether (R-O-R)
b. Ketone (R-CO-R) & Aldehyde (R-CHO)
c. Carboxylic acid (R-COOH) & Esters (R-COOR)

Stereoisomers
Stereoisomers
-Have the same bonding pattern
- but different arrangement of atoms in 3 –D space
Three Classes of Stereoisomers:
1. Conformational/Conformers
2. Geometric Cis/Trans Isomers
3. Optical Isomers

Stereoisomers: Conformational
Conformational Isomers- different arrangement of atom that
can be converted into one another by rotation about a
single bond.
- Exhibited by:
1. Alkanes
2. Cycloalkanes
- Newman projection can show 3 conformations:

1. Eclipsed
2. Anti-staggered
3. Gauge-staggered

Stereoisomers: Conformational
Factors Affecting Stability of Conformers:
1. Tortional Strain
- Occurs due to eclipsing bonds
- repulsive in nature that causes destabilization
2. Steric Strain
- occurs due to bulky/big alkyl groups
- also repulsive in nature that causes destabilization
•Stability: anti-staggered > gauge-staggered > eclipsed

Stereoisomers: Geometric Isomers
- Different arrangement of atoms due to geometric restraint
(double bond or ring).
- Can be exhibited by alkenes and cycloakane
a. Cis isomer- similar atoms on the same side

b. Trans isomer - similar atoms on the opposite side
a a a b
C C C C
b b b a
2 kinds of
Cis Trans atoms
Note: There should be 2 different atoms attached to the C with
double bond

Draw the cis and trans isomers of the ff:
1. but-2-ene
2. pent-2-ene
3. 1,2-dimethylcyclobutane

Learning Check
Write YES if there is cis and trans isomerism then, draw the
cis and trans. Write NO if there is no isomerism.
___1. 1-butene
___2. 1-chloropropene
___3. 2-hexene
___4.2-methyl-2-butene

• If there are 4 different groups attached to the double bond,
use the E and Z system.
H3 C CH 2CH 3 H3C Cl
C C C C
Cl Br Br H
• Z- groups with higher atomic no. on the same side of the

= bond
• E- groups with higher atomic no. on the opposite side
Priority Group:
1. Higher Atomic #, higher priority
2. Ξ > = > -

Stereoisomers: Optical Isomers
- Arises due to the presence of a CHIRAL carbon or
asymmetric carbon.
What is a chiral carbon?

- a carbon attached to four different groups atoms
H3C C CH2CH3
OH

• For every chiral carbon, 2 isomers can be drawn,
CH3 CH3
H C OH HO C H
CH 2CH 3 CH 2CH 3
•Are these 2 molecules the same?______No

•What is their relationship?They are mirror image  they
are not superimposable

• Two molecules w/ mirror image relationship but are not
super imposable are called: Enantiomers
•Not an enantiomer if they can be superimposed.
R & S System:
1. R - If priority groups decreases in clockwise
2. S - If priority groups decreases in counterclockwise

Learning Check
•Name the following compounds
H H
1. C C Cis-1,2-dichloroethene
Cl Cl
H Br
2.
C C Trans-1,2-dibromoethene
Br H

PROPERTIES OF ORGANIC
COMPOUNDS

Physical Properties of Organic Compounds
•Physical
•1. Melting Point
•2. Boiling point
•3. Solubility
•Chemical
•1. Acidity
•2. Basicity
•3. Aromaticity

REVIEW!!! IMFA / IPFA
•IMFA: InterMolecular Forces of Attraction
•IPFA: InterParticle Forces of Attraction
Particle: can refer to molecules and Ions
Types of IMFA?
1. Ionic/ Electrostatic Attraction
2. Dipole-Dipole Interaction
3. H-Bonding
4. LDF- London Dispersion forces

Ionic
1) Ionic/ Electrostatic Attraction
- the strongest interaction
- + -
H+A- + B+OH- ---> B+A- + H+OH-
Examples of Organic Salt:

1. Salts of RCOOH (Carboxylic Acid)
2. Salts of Phenol

Dipole-dipole
2. Dipole- Dipole Interaction
- weaker than ionic
- has dipole (one end is +; the other end is -)
+ - + -
+ - + -
Examples of D-D:
• Carbonyl Compounds – contain carbonyl group

Hydrogen Bonding
3. H-Bonding
- An electron poor H+ attached to EN atom like F,O,N
- H+ is attracted to a LP
•Reciprocal H-Bond:
-a compound should have an H + and an atom with a LP.
Reciprocal - it can give and accept a H +

Hydrogen Bonding
•What are examples of Molecules displaying H-bond?
O O
> R OH > > R NH2
R C O H R C NH 2
sp3
sp2
•Strength of H-Bond
- The more positive the H, the Stronger the H-Bond it
forms.

London Dispersion Forces
4. LDF
-Weakest of all interaction
- present in all molecules
- the only IMFA in non-polar molecules (Hydrocarbon &
Symmetrical molecules)

Factors Affecting the Strength of LDF
1) Size of the molecule
- The bigger the size, more forces, the stronger the LDF
–C3H8 C5H12
2. Branching- among isomers

- More branched; small contact area; weaker interaction;
weaker LDF

Learning Check
•Identify the IMFA: Choices a)ionic b) dipole-dipole c)
H-bond
•Compare the strength of IMFA in each of the following pairs

1. Melting point
-Solid and liquid are in equilibrium
solid liquid
-To melt: a need to break the interaction
2. Boiling Point
- Temperature at which the vapor pressure of the liquid = to
the atmospheric pressure
- To boil: need to break the IMFA

Factors that affect the MP and the BP:
1. Molecular Weight:
- MW; IMFA; BP and MP
2. Branching Among Isomers

More Branch: IMFA; BP and MP
3. Intramolecular H-Bond
- Presence of intra-molecular H-bond prevents it from
engaging in intermolecular H-bond  IMFA, BP and MP

4. Polarity
-More polar groups ; IMFA; BP & MP
Ex. Polar Groups

-OH -NH2 - C=O
5. Symmetry
-Symmetrical molecule – are Nonpolar compounds
- NP; IMFA; BP and MP

Among Molecules:
>
Salts RCOOH> ROH> RNH2 > RCHO RCOR > ROR > R-H
LDF
Ionic H-bond Dipole-
dipole

3. Solubility
- Involves breaking the interaction and forming a new
interaction among solute and the solvent.
―LIKE DISSOLVES LIKE‖
What if we mix Nonpolar molecules w/ water?
O O H H O
H H H H H H
O
+
Hexane -LDF H2O- H-bond •No attraction

• no mixing
NO resulting IMFA
Factors Affecting Solubility
1. Nature of the solute
2. Nature of the solvent
3. MW/ size
4. Effect of Bonding
5. Intramolecular H-Bond
6. Polarity
7. Symmetry

1. Nature of the solute
• I. Ionic Salts
- IMFA: Ionic
- Very soluble in water
-E.g. Organic salts
• II. Hydrocarbons
- IMFA: LDF
- Nonpolar; insoluble in H2O
- E.g. Hydrocarbons

• III. Polar- w/c can have reciprocal H-Bonding
• IMFA: H-bond; soluble in H2O
H3C O
C > R O H > R NH2
O
OH
• IV. Polar- can H-Bond with H2O

• IMFA: dipole-dipole R
R C O R C O
O R N
H > R > R R
> R
•Note: If R is small (< 5 carbons), these are water soluble.

2. Nature of the Solvents:
a) Polar Solvents O
O H3C CH2 OH
H3C CH2 OH C
H H H3C CH3
CH3
b) Non-polar solvents
CH3
CH 2 CH 2
Hexane
H3C O CH3
toluene Diethyl ether

3. MW/Size
C C C OH Most Soluble in H20

C C C C OH
C C C C C OH Least Soluble
• MW ; Solubility in H2O
Why? As the size of the R inc, the molecule becomes more

nonpolar.

4. Effect of Branching
C
C C C OH C C C C C OH
MORE POLAR
Note: Branching; LDF, more polar, soluble in H2O

5. Intra-molecular H-Bond
-Presence of Intra; solubility in H2O
6. Symmetry
- Symmetrical molecules are NP,  insoluble in H2O

Chemical Properties of Organic Compounds
Concepts of Acids and Bases
1. Arrhenius
ACID – dissolves in water to produce H+
BASE- dissolves in water to produce OH-
Acids Bases
1. HCl 1. NaOH
2. HNO3 2. NH4OH
React: Acid + Base Salt + Water

ACIDITY
2. Bronsted- Lowry
ACID – H+ donor
BASE- H+ acceptor
O O
+
C H + O C O
H3C O H H H3C O-
+ H H
H
Acetic acid water Acetate ion Hydronium ion
- A proton donor - A proton acceptor Conjugate Base Conj Acid

- An ACID - A BASE

ACIDITY
ACID- proton donor
- H+
ACID CB
Base- a proton acceptor

+H+
Base CA
NH3 + H2O NH4+ + OH-

ACIDITY
Give the conjugate base:
1. H2O
2. HCOOH
3. CH3CH2OH
Give the conjugate acid:

1. NH3
2. RCOO-
3.CH3O-

ACIDITY
Lewis Concept:
Acid - e- pair acceptor
Base – e-pair donor
.. Lewis Base: Can

RNH2
.. > NH
.. 3 > CH3OH
.. donate
Cl H F
Lewis Acid: All

Cl Al H B F B central atom have
incomplete octet and
can accept a LP
Cl H F

AACIDITYcidity
Acidity - explained in terms of Bronsted-Lowry Concept
Strength of Acid
-depends on the tendency to lose the H+
Thus, Strong Acid= tendency to lose a H+

Weak Acid = tendency to lose a H+

ACIDITY
How do we measure the strength of an acid?
-Through pKa
- pKa= - log (Ka)
note: Ka- acid ionization constant
- Thus, Ka, pKa then, strong acid
Ka, pKa, then weak acid

ACIDITY
Acids pKa
RCOOH 4-5 STRONGEST Phenol 10
HOH 15.7 ROH 16-17 WEAKEST
Functional Group Example pKa

Alkane CH4 ~50
Amine NH3 ~35
Water H2O 16
Protonated Amines NH4+ 10
Carboxylic Acids CH3COOH 5

Factors Affecting Acidity
1. Positivity of the H
- The more + the H, the more easily it is lost,  more acidic
Ex. Carboxylic acid and Alcohol
2. The bulkier the -R, the stronger the e- release, the less +
the H
Ex. t-butyl alcohol and 1° alcohol

3. Inductive Effect
- Presence of e- withdrawing group (-I) near the acid group
(H+), acidity σ+
σ+
H3C CH2 CH OH H3C CH2 CH2 OH
.
Br
-I Br
-I
A B
• The more the EN the atom near the acid group (+H),
the stronger the –I, thus, more + is the H.
ACIDIC
Ex: CH3CH2OH ___ CF3CH2OH

4. Hybridization- The higher the s character, the more
acidic.
ethyne > ethene > ethane
5. EN atom bonded to the H

a. Within the period: C < N < O< F
EN: Inc from L to R
Note: EN atom; - I; Hσ+;  Acidity
σ+
σ+ σ+ σ+
C-H N-H O-H H-F

b) Within a family
- The more stable the CB, The STRONGER the ACID
ACID CB
H-F F-
Cl-
H-Cl
Inc in acidity Inc stability of CB
Br-
H-Br
I-
H-I

BASICITY
-Basicity depends on the availability of the LP
-The more available, the more BASIC
..
O
.. ..
H N H
H H <
H
- O is more electronegative,  less e- donating than N

BASICITY
..
NH2
..
< R NH2
• Aromatic amines are less electronegative due to

resonance . LP is not available.
Note: e- releasing groups (alkyl) ; Basicity

e- withdrawing (EN atoms) ; Basicity

BASICITY
Which is a stonger base?
NH2 R N H
Note: e withdrawing ; Basicity (Reason: LP is less

available)

AROMATICTY
- Displayed by aromatic compounds
- It gives stability to the compound due to resonance.
-Criteria for a compound to be aromatic (STABLE)

1. CYCLIC
2. All atoms in the ring are sp2
3. W/ an odd number of  e- pairs
4. Obeys the 4n+2 rule
4n+2= no of  e- is applied and if n=0 or a positive
integer

AROMATICTY
Which are aromatic?
N
H
..N H
N
..

ORGANIC REACTIONS

Introduction to Organic Reactions
Substrate + Reagent  Intermediate  Products
(Reactant) 2 kinds: 3 kinds of C intermediate:
-org molecule 1. E+ 1. Free radical .
. C .
2. Nu-
.
2. carbocation +
. C .
•E+: Electrophile 3. carbanion .
..-
•Nu-: Nucleophile . C .
.

Substrate
ORGANIC molecules contain a REACTIVE SITES (site
attracted by the REAGENTS).
O
R CH CH2
REACTIVE
SITES R C H
R C CH
σ+ O
σ-
R CH2 O H
R C R
σ+ σ-
R CH2 X

Aromatic
H - all C are the same
H H
- all 6H are the same
H H Reactive site: the ring or the H
H
Where is the reactive site?

Reagents
Reagents- attack the organic molecule at the reactive sites.
2 Kinds Reagents:
1. Electrophiles, E+ - e- loving reagent, e- poor
Electrophiles can be H+
1. + charge
Br – Br  2 Br
2. e- deficient, like Free radical
Cl
.
Fe Cl
3. Incomplete octet ex. lewis acid
Cl

Reagents
2. Nucleophile, Nu-
- love the nucleus (+), e- rich
Nucleophile can be:
1. – charge
2. Could be neutral compound with LP (e- rich)
X-
..
Ex. NH3
HO-
.. e- rich because of the LP
RO- H- O- H
.. ..
R O H
..

Learning Check
Identify if an E+ or Nu-
..
___1. CH3NH2 ____6. +CH3
___2. NH2- ____7. :CH3
___3. Ag+ ____8. . CH2CH3
___4. AlCl3 ____9. CH3 -O-H
___5 I. ____10. C H
H

2 ways a bond breaks (Bond Cleavage)
1. Homolytic- bond breaks equally
- promoted/initiated by light, UV, or heat.
Ex. UV
A B .A + .B
E+ E+
Free radicals  are derived from a homolytic bond

cleavage

2 ways a bond breaks (Bond Cleavage)
2. Heterolytic  bond breaks unequally
A B A+ + :B-
CATION ANION
• Homo- will give FR products

• Hetero- will give + cation and- anion products

Carbon Intermediates
1. Carbon Free Radical
- E+ .
. C .
- 3 classes
.
1 °, 2 °, 3 °
Which one is the most stable?
Order of Stability:
3>2>1> methyl free radical
. . . .
H3C C CH3 H3C C CH3 H C CH3 H C H
CH3 > > H

> H
H

+
2. Carbocation . C .
- E+ .
- 3 Classes: 1 °, 2 °, 3 °
- Order of Stability 3 ° > 2 °>1 °> methyl carbocation

3. Carbanion . ..C - .
-It is a carbon with. a LP and is (-) charged
-3 classes: 3°,2°,1°
- order of stability: :-CH3>1°> 2°> 3°
.. - .. - .. - .. -
H C H H C CH3 H3C C CH3 (CH3)C
H H H

REVIEW
Classify all the following carbons into 1°,2°,3°
1.
CH2 CH3
2.
H3C CH CH2 CH3
3. CH3

Compare the stability by writing > or < between two
structures .. -
.. -
1. CH3- CH2< CH3
CH3
. .
>
2.
+ +
CH CH3 > CH2 CH2
3.
+ +
CH2 < CH 2
4.

Learning Check
Give the E+ and the Nu-
1. H---Cl
2. Cl---Cl
3. H---O---H
4. H---NH2
5. HO—NO2

Types of Organic Reactions
1. Addition Reactions
2. Elimination Reactions
3. Substitution Reactions
4. Acid-Base Reactions
5. Reduction- Oxidation Reactions

1. Addition Reactions (A)
. C . . C . . C C .
.
. .
4 max 3 groups 2 groups
groups (unsaturated) (unsaturated)
Addition Rxn - undergone by compounds that

are unsaturated
- Results to increase in the no. of atoms bonded to C
H H
Pt
H2C CH2 H2 H C C H
+
Hydrogenation H H
.

1. Addition Reactions (A)
Example 2:
H2 H2
HC CH
Pt Pt
ethyne ethene ethane
• Once it is saturated, it can no longer add in the compound.

H
H3C CH2Cl
Cl
H2C CH2 + H Cl
H2C CH 2 or

2. Elimination Reaction
-Is the opposite of Addition (E)
Conc H2SO4
H3C CH2 OH H2C CH2 + H O H
Δ
dehydration
-This reaction is called:____________
In Elimination:
1. Substrate is SATURATED
2. Product is unsaturated
Example of Elimination: Dehydration of Alcohol

3. Substitution Reaction
-A reagent replaces a group in the reactant
H3C CH2 Br + OH - H3C CH2 OH + Br -

4. Acid Base Reaction
• Neutralization reaction
H
+ O
R O H
+ H+ Cl- R O H
H + R+Cl-
H
ACID
Protonation of OH

5. Reduction-Oxidation reaction
-REDOX- Reduction and Oxidation
•Reduction:
-Gain of e- (Inorg)
- Gain of H or loss of O or sometimes both (Organic)
- undergone by Oxidizing Agent
•Oxidation:
-Loss of e- (Inorg)- Inc in the oxidation num.
-Gain of Oxygen, loss of H or Both
- undergone by Reducing Agent

5. Reduction-Oxidation Reaction
K2Cr2O7 K2Cr2O7
H3C CH2 OH
H2SO4 H2SO4
-K2Cr2O7 – Yellow Orange

-Cr3+ - color is Blue Green
•Alcohol- is being oxidize by enzymes in our body.
•Aldehyde  acetic acid ( reaction is very slow)

5 Reduction-Oxidation Reaction
H3C CH OH K2Cr2O7 O
CH3 H2SO4 H3C C CH3
Isopropyl alcohol Acetone/ propanone
CH3
K2Cr2O7
H3C C OH No Reaction
H2SO4
CH3
- 3° OH cannot be oxidize

REACTIONS OF
ALKANES AND CYCLOALKANES
Reaction of Alkanes and Cycloalkanes
- Least reactive molecules.
- Undergo Free Radical Electrophilic Substitution (SFR).
- Forms FR intermediate
- Stability (3°>2°>1°)
General Reaction: UV
R-H + X-X  R-X + H-X
Alkane Halogen
UV
CH4 + Br2  CH3Br + HBr

Reaction of Alkanes and Cycloalkanes
Mechanism
-It is a series of steps shown in the reaction.
1. Initiation- formation of X .
2. Abstraction of the H from the alkane by the X .
3. Termination

Electrophilic Substitution Reaction
UV
H3C CH2 CH3 + Br-Br
Stability of radical: 3° > 2° > 1 ° > CH3 °

. H3C CH2 CH2 + H-Br
H3C CH2 CH2Br
H3C CH2 CH3 .Br

H3C CH CH3 + H-Br
H3C CHBr CH3
More stable

Learning Check
Give the major product (More stable product)
1. UV
CH3CH3 + Br2
2. UV
+ Cl2
3. H UV
+ Br2
CH3
4. UV
H3C CH2 CH CH3
+ Cl2
CH3
5. CH 2
UV
CH3 + Br2
REACTIONS OF UNSATURATED
HYDROCARBON

Reactions of Unsaturated Hydrocarbons
-Alkenes
- Alkynes UNSATURATED
-Cycloalkenes
-Cycloalkynes
Unsaturated compounds- will undergo Electrophilic Addition

Reaction (AE)
E Nu
- E+. enters first,
. then the Nu-
H C C H
C C + E+ Nu-
H H
. .
Inc # of atoms bonded to C

Example:
H H
C C + H+ Cl-
H H

Substrates for AE
 The unsaturated compounds could be:
A. Symmetrical B. Unsymmetrical
H3C CH CH2
H2C CH2
HC CH H3C C CH
CH3
H3C CH CH CH3

Reagents: ( are added to the = or  bond)
A. Symmetrical
Ex. 1) H2 in Pt or H2 in Ni or H2 in Pd
2) X2 in CCl4 (solvent) e.g Br2 in CCl4
B. Unsymmetrical
H-X (e.g.) H—Cl, H—Br, H—I
H—OH ; H—OSO3H (sulfuric) or H2SO4

Electrophilic Addition Reaction
Examples of AE
1) Change = bond into – bond
1. HYDROGENATION 2) Add reagent 1 per C
•For Alkenes
+ Pd H2C CH 2 H3C CH3
H2C CH2
+ H2
H H
•For Alkynes
-Change the  bond into =, the = into –H H
H3C C CH+ H2 + Ni H3C C CH + H2 + Ni
H3C CH2 CH3

Br
2. HALOGENATION
CCl4 H3C CH CH2
H3C CH CH2 + Br2
Br
•Br is bulky ( unstable)  opposite sides

Br
CCl4 + Br2 CCl4
+ Br2 HC CH
HC CH
Br
Br Br
H3C C C H
Br Br

3. ADDITION of H-Y
• H-Y can be (H-Cl, H-Br, H-I, H-OH)
OR
H2C CH2 + H-Cl CCl4 H2 C CH2 H3C CH2Cl
H Cl
symmetrical

H3C CH CH2 + H-Cl 2 answers
H3C CH CH 2 H3C CH CH 2
Cl 1° 2°
H
Cl H
Minor product Major product
• Note: If alkene is unsymmetrical, decide the major and

minor product.
• Major product: Most stable intermediate

•To predict the major product:
•Markovnekov’s Rule: The E+ (H+) always goes to the C

with more H while the :Nu- (Cl-) goes to the C with less H
CH3 H CH3
H3C CH C + H+ Cl- H3C C C CH3

CH3
H Cl

• Markovnekov’s Rule in  bond: Br H
H3C C C H + H-Br H3C C C H

(Excess)
Br H Br H
H3C C C H + H-Br H3C C C H
Br H

Learning Check
CH3
1. 5.
+ H-Br H3C CH2 CH C CH3 + H-I
2. + H-Cl 6. CH 2 CH3 + H-OH
CH3
3. Br2
H3C CH2 CH C CH3
CCl4
Pt
4.
H2
(excess)

4. Addition of H2O to Alkynes: Keto enol
-Proceeds only to Alkyne
- the product ENOL tautomerizes to KETO form
- follows Markovnekov’s rule
* Tautomers- isomers that differ only in the location of the H.
OH ENOL
H2SO4
H3C C CH + H+OH- HgSO4 H3C C C H
(catalyst)
:
H
: OH
: O : H
H3C C C H H3C C C H
H H

OH H
C C H
H2SO4
C CH ENOL
+ H2O HgSO4
O H
C C H
Give the products of hydration H KETO

using the ff. substrates.
Acetophenone
HC CH

REACTIONS OF AROMATIC
HYDROCARBONS

Reactions of Aromatic Hydrocarbons
• Benzene ring: H H
- Aromatic
H H
- Resonance, 6 C’s are equivalent
6H’s are equivalent H H
- Although unsaturated, it will not undergo AE due to

stability.

Reactions of Aromatic Hydrocarbons
E Nu
AE
+ E+Nu- Not aromatic
- No longer stable
Aromatic
- stable
• Will undergo Electrophilic Aromatic Substitution

H
E
SE
+ E+Nu-
+ H+Nu-
Aromaticity is
preserved

Electrophilic Aromatic Substitution
-The reaction generates E+
1. Nitration +
Reagents: HNO3 + H2SO4  NO2 + HOH + HSO4-
2. Sulfonation: +
Reagents: SO3 +H2SO4  SO3H + HSO4-
+
3. Halogenation:
Reagents: X—X + FeX3  X + FeX4-

Electrophilic Aromatic Substitution
4. Freidel-Craft’s Alkylation +
Reagents: R—CH2—X + AlX3  R—CH2 + AlX4-
5. Freidel-Craft’s Acylation
O O
Reagents:
R C X + AlX3 R C . + AlX4-
+
General Reaction:
H E
+ E+Nu- + H+Nu-

Give the E+
1. H3C CH Br
+ AlBr3
CH3
2. Br—Br + AlBr3
3. CH 2 Br + AlBr3
O
4. + AlCl3
C Cl

Learning Check
1.
H3C CH Br
+ + AlBr3
CH3
O
2
+ H3C CH2 C Br + AlBr3
3. + HNO3 + H2SO4

Learning Check
4.
+ Br2 + AlBr3
5.
+ CH3Cl + AlCl3
CH 2 Br
AlBr3
6.
+ O
C Br
AlBr3
7.
+
REACTIONS OF ALCOHOLS

Reactions of Alcohol
1. Oxidation
OA: K2Cr2O7 – will be reduced to Cr3+
Y.O B.G
a) [O] [O]
R CH2 OH R CHO R COOH
1°OH ALDEHYDE CARBOXYLIC
ACID
O
[O] [O] O
H3C CH2 OH
H3C C H
H3C C OH
Ethyl alcohol acetaldehyde Acetic Acid
HANGOVER Not toxic

b) OH O
SUMMARY:
[O]
R CH R R C R
1°OH - is oxidized into
KETONE aldehydes & carboxylic
OH acid.
O
[O] 2°OH - is oxidized into
H3C CH CH3 H3C C CH3 Ketone.
isopropyl alcohol Acetone 3°OH – NO RXN
OH
c) [O]
NO RXN
R C R

Why is CH3OH toxic?
-Because the product formed after oxidation is TOXIC.
O O
[O] [O]
CH3OH H C H H C OH
Formaldehyde Formic Acid
(Formalin) (Ant’s Bite - Blindness)

2. Dehydration of Alcohols
Dehydrating Agent:conc. H2SO4
Reaction Involved: Elimination
Product Formed: Alkene
OH
H3C CH CH3
H2SO4 H3C CH CH2
σ β - H2O
1. Remove –OH from the σ C

2. Remove H from the β C
3. Create = bond bet σ and β

OH
H3C CH 2 CH CH3
β σ β
H2SO4
H3C CH CH CH3 H3C CH2 CH CH2
-Saytzeff’s Rule- States that the major alkene (the more

stable alkene) is the alkene with more alkyl groups

Predict the Product of Elimination reaction of conc H2SO4.
OH
β β H2SO4
H3C CH CH CH3
σ
CH3
HO H
H2SO4
HO
CH3
H2SO4

Reactions of Alcohols
3. Replacement of Acidic H with Na Metal
-Order of reaction: 1°>2°>3°
SE
R CH2 O H + Na R CH2O- Na+ + H2
4. Nucleophilic Substitution (SN)

- Lucas Test (Lab)
- Reagent: H-Cl in ZnCl2
.. ZnCl2
H3C CH2 OH
.. + H-Cl H3C CH2 Cl
Catalyst
+ H-O-H

Nucleophilic Substitution Mechanism
1. For 3 ° and alkyl halide – SN1 (Substitution Nucleophilic
Unimolecular
- Two-step reaction: bond breaking before bond forming
Step 1: slow step: bond breaking
Step 2: bond forming
2. For 1° Alcohol and alkyl halide- SN2 (Substitution

Nucleophilic Unimolecular)
- One- step reaction: Formation of TS ( involves substrate
and nucleus)

Factors Affecting SN Reactions
•.1. Nature of Substrate
- Stability of C+: 3° > 2 ° > 1 ° > CH3 °
2. Nucleophile
- SN : Nu not involved in rate-determining step
1
-
- SN : Nu is involved in RDS. Needs a strong Nu to

2
- -
displace leaving group.

REACTIONS OF CARBOXYLIC ACID
AND DERIVATIVES

Acid Derivatives
In order of dec Reactivity: O
1. Acid Chloride (highest reactivity)R C Cl

O O
2. Anhydride R C O C R
O
3. Esters
R C O R
O
O
4. Amide R C NH2
R C .
•Why are they acid Derivatives? Contains the acyl grp

General Mechanism
O
O-
R C L + H+Nu- R C L
Nu
+ -
R C Nu + H L
•This Rxn is called: SN (Nucleophilic Acyl Substitution)

Leaving Ability
•. O
Cl- > -O C R > -OR > -NH2

-strongest -least tendency
tendency to leave
to leave
- Through protonation, it will

be a good leaving group.
• Note: The strongest/very reactive acid derivatives can

form less reactive acid derivatives.

Reactions of CA and Derivatives
R C L + H+Nu-
Leaving Group: Reagents

ROH H+ OR-
-Cl
O
HOH H+ OH-
-O C R
NH3 H+ NH2-
-OR
-NH2

Acid Halide
O
+
H3C C O- Na
O
CH3O-H (H+ OCH3)
H3C C Cl
HO-H (H+ OH- )
NH3 (H+ NH2- )

Acid Halide
O
+
H3C C O- Na
O
CH3O-H (H+ OCH3)
H3C CH 2 C Cl
HO-H (H+ OH- )
NH3 (H+ NH2- )

Acid Anhydride
HO-H
O O
CH3O-H
R C O C R
NH3 (H+ NH2- )

Acid Anhydride
HO-H
O O
C O C
CH3O-H
NH3 (H+ NH2- )

Esters
HO-H (H+ OH- )
(H+ ( acid ) acid

catalyzed
O
HO-H
H3C C OCH2CH3 (NaOH) ( base )

Base catalyzed
NH3 (H+ NH2- )
(ammonolysis)

Amides
• Amides – least reactive
- will only undergo hydrolysis O
HO-H (H+ OH- )

R C OH
O
(HCl) + NH4+Cl-
R C NH2
O
HO-H NaOH
+
R C O- Na
+ NH3

Amides
HO-H (H+ OH- )
O (HCl)
C NH2
HO-H NaOH

“BELIEVE THAT YOU CAN
AND YOU”RE HALF-WAY THERE.”

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ORGANIC CHEMISTRY

Ex. of C containing compound w/c are not ORGANIC

Organic Chemistry MCL2018 2

• If bond – based on ΔEN

sugar Hexane (gasoline)

Organic Chemistry MCL2018 3

Organic Chemistry MCL2018 4

Organic Chemistry MCL2018 5

How many isomers?

Organic Chemistry MCL2018 6

• Exercise in Lewis structure:

Organic Chemistry MCL2018 7

Organic Chemistry MCL2018 8

Organic Chemistry MCL2018 9

Organic Chemistry MCL2018 10

Organic Chemistry MCL2018 11

• Elements other than C can

two nonbonding electrons, and

Organic Chemistry MCL2018 13

• The oxygen atom is sp -hybridized

• Oxygen has six valence-shell electrons but forms

• The H–O–H bond angle is 104.5°

Organic Chemistry MCL2018 14

Organic Chemistry MCL2018 15

- the more unequal the sharing of e-, the stronger the

Factors affecting bond polarity

Organic Chemistry MCL2018 16

So, ΔEN : BP ( the more the unequal is the sharing)

H= 2.1 C=2.5 N=3 O=3.5 F=4.0

Organic Chemistry MCL2018 17

FCA = (Group No. of A) - ½(bonding e-) - (e- in the LP)

FC = + (gives away e-, e- poor), polarity enhanced

Organic Chemistry MCL2018 18

1. Which N-H bond is more polar?

2. Which OH is more polar?

Organic Chemistry MCL2018 19

Which is more polar?

Note: the more EN the atoms are around the C, the

Organic Chemistry MCL2018 20

•Note: higher s character = more EN, therefore the more

Organic Chemistry MCL2018 21

Which is has higher Bond Energy?

Organic Chemistry MCL2018 22

Factors affecting bond length:

Organic Chemistry MCL2018 23

Organic Chemistry MCL2018 24

Organic Chemistry MCL2018 25

Organic Chemistry MCL2018 26

Organic Chemistry MCL2018 27

Organic Chemistry MCL2018 28

• Aromatic hydrocarbon has a benzene ring (d).

Organic Chemistry MCL2018 29

Pentane has 5 carbon atoms and 12 (2 × 5 + 2 = 12)

Organic Chemistry MCL2018 30

Organic Chemistry MCL2018 31

Organic Chemistry MCL2018 32

The suffix name (ane) is changed to -yl.

Organic Chemistry MCL2018 33

Organic Chemistry MCL2018 34

3. Multiple, identical branches use di (2), tri (3), tetra (4) to

4. Name the branches in alphabetical order, separate

H3C CH2 CH CH CH CH3

6. When 2 different groups compete for the same position,