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GENERAL OVERVIEW

Organic Chemistry  History

 Jons Jacob Berzelius  “organic”
 “Vital Force Theory” or “life-force theory” 
organic compounds ONLY originate from
living things
 Friedrich Wohler
 Ammonia + cyanic acid  urea
 Torbern Bergman  org vs inorg
 So what is ORGANIC CHEMISTRY?
Free Powerpoint Templates
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By: Rowel P. Catchillar

ORGANIC VS INORGANIC Characteristics of CARBON

PROPERTY ORGANIC INORGANIC
Flammability Flammable Not flammable
Boiling point Low High CATENATION – ability to bond
Solubility in water Insoluble Soluble successively to other carbon atoms to
Solubility in non-polar Soluble Insoluble
solvents form chains and rings of varying sizes
Covalent Ionic bonding
Types of bonding
bonding
Isomerism Exhibit Does not exhibit
Atoms per molecules Several Few
Structure Complex Simple
Electrical conductivity Poor Good

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Can you identify the type

HYBRIDIZATION- mixing of 2 or more non- of hybridization?
equivalent atomic orbitals to form new set
of equivalent orbital

TYPES:

sp3
sp2
sp

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Remember Me!

 Bond angle
 Bonds
 Steric number & Shape prediction

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Bond Angle Bond types

 Sigma bond: the first bond

 Single bond
with any other atom
 Double bond
 Pi bond: any 2nd and third
 Triple bond
bond with any other atom

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Shape Prediction
 Steric number =  + lone pair
 Based on VSEPR Theory

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Shape Prediction The Functional Group

 Predict the shape of:
 H2O  Significance??
 NH3  The chemistry of every molecule
 CH4 is determined by the functional
group it contains

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The Functional Groups

Exercise #1: Functional Group
Determination
Amine Alcohol
 Aspirin
Ketone Amide
 Penicillin nucleus
Ester Carboxylic
acid

Alkyl Halide Aldehyde

Ether
Hydrocarbons
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The Carbon Atom NOMENCLATURE SYSTEM

 Contains 4 binding sites for other atoms to  Common
attach to it.  Usesthe name given when it was
 These four binding site, when bonded with discovered
other atoms/molecules form a tetrahedron.  Uses the source: wood alcohol
 Found in Group 4, Period 2  Uses prefixes: -n, –iso, -neo
 Atomic number 6  Derived name
 1s2 2s2 2p2
 derived from a parent compound
 Needs 4 more electron to complete its octet
 Valence: 4  IUPAC
 Neither donate nor accepts electron
 Most systematic
 Can only share: covalence  Eg. 2-methylhexane
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IUPAC System Prefixes HYDROCARBONS

 Composition
No. of C Prefix No. of C Prefix  Combustion process
atoms atoms
 Types
1 6
 Aliphatic(straight or branched;
2 7 saturated or unsaturated)
3 8  Aromatic
4 9  Alicyclic or carbocyclic
5 10

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Derivatives Saturated Hydrocarbons

Halogen -containing Alkanes or _______
Alkyl halide
 SINGLE BOND ONLY
Aryl halide
 General formula: __________
Oxygen -containing
Alcohol, phenol, ether, aldehyde and ketone,  Type of bond: __________
carboxylic acid and derivatives  Suffix: -ane
Nitrogen- containing Alkyl group: removal of 1 hydrogen; ends
Amines and amides with –yl
Sulfur containing  Example:Methane (when 1 hydrogen is
Thiols or ________ removed: _______)
Thioethers
Thiophenols
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Nomenclature Examples
Determinethe longest possible chain
Examples: 2,3-dimethylpentane:
and name the corresponding alkane correct or incorrect?
name
1,2-dimethylbutane: correct or
Substituents are numbered with the incorrect?
lowest position number 4-methyl-3-ethyl-octane: correct or
If
2 or more substituents are present, use incorrect?
prefixes di-, tri-and so on.
When several different alkyl groups are
attached to the parent chain, use
alphabetical arrangement Page 23 Page 24

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Saturated HC Nomenclature

Cycloalkanes  Additional Rule in Naming Cycloalkane

Carbon rings; can be written in geometric  Step1: Use the cycloalkane name as the
figure parent chain.
General formula: ______________  Step 2: Number the substituents starting at the
named with the prefix cyclo- in front of the group that has alphabetical priority, and
corresponding alkane name proceed around the ring in the direction that
gives the second substituent the lower
possible number.

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Introduction to  Elimination reaction

reaction mechanism  Opposite of addition reaction
 Single reactant splits into two products
 Reaction mechanism – a process by
 Ex: chloroethane
which a chemical reaction occurs.
 Substitution reaction
 Two reactants exchange parts to give two new
1. Addition reaction products
 Two reactants react together to form a  Ex: methane + chlorine
single new product with no atoms “left  Rearrangement reactions
over”
 Single
product undergoes a reorganization of
 Ex: CH3CH=CH2 + HCl bonds and atoms to yield a single isomeric
products
Page 27  Ex: conversion of cis-butene to trans-butene Page 28

Unsaturated HCs IUPAC Naming

 Nomenclature:
 Alkenes or _______
 Double bonds  Determinethe longest change having the
 Bond angle: _______
DOUBLE bond
 Type of bond: _______  Number the longest continuous chain so
 General Formula: __________
the double bond will receive the lowest
possible number
 Same nomenclature as alkane but change –ane 
-ene  Ifmore than one same substituents are
present, use prefixes di-, tri- tetra- and so on.

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Unsaturated HCs
 Cycloalkenes
 Alkadienes: 2 carbon-carbon double  Carbon ring with double bond
bonds;  General Formula: __________
 indicate the position of double bond +  Alkynes or _______
prefix + diene
 Triple bonds
 1,3-butadiene  Bond angle: ________
 Isoprene units  Type of bond: ________
 General Formula: _________
 Same nomenclature as alkane but change –
ane  -yne
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Aromatics Huckel’s rule of aromaticity

 Pleasant
odor possessed by there substances (this
meaning has been dropped)
4n + 2 = πe (electrons in double bond);
 Benzene is the parent substance >> Isolated by
____________ in 1825.
if n is whole number, then aromatic!
 Accordingto August Kekule, carbon atoms in a Benzene: Aromatic or not?
benzene molecule are arranged in a six- What is the name of the compound/s if πe
membered ring with one hydrogen atom bonded = 10?
to each carbon atom and with three carbon-
carbon double bonds Cyclobutadiene: aromatic or not?
 Orbital hybridization is sp2.
 Forconvenience, benzene is written either in the
following ways…

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Alcohols
 Classification
 Based on the # of R bonded to the carbon
bearing the –OH group (C – OH, carbine
ALCOHOLS, PHENOLS, THIOLS, AND group)
ETHERS  Primary
 Secondary

 Tertiary

 Based on the # of –OH groups

 Monohydric

 Dihydric

 Polyhydric
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 Nomenclature: CH3CH2CH2OH
 Common names  IUPAC:

 Name of alkyl group + alcohol  Derived:

 CH3OH  Common:

 Derived
name: carbinol (an old name of
methanol) CH3CHCH3
 CH3CH2OH I
 IUPAC rules : similar to alkanes OH
 Include –OH group in the parent chain  IUPAC:
 –OH is given the lowest possible number  Derived:

 Name ending in –ol.  Common:

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 Examples of alcohol
Reactions of Alcohol
 Methanol / _______ alcohol
 Relate the mechanism of toxicity
 Antidote: ________ or ________
 Ethanol
 Correlations:
 Bakit malaki ang tian ng pulis? d:]
 Bakit “makapal ang mukha” ng lasing?
 Inducer or inhibitor?

 Isopropyl alcohol
 Ethylene glycol
 Glycerol
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 Oxidation
Alkanes  Alcohols (10 or 20)   Dehydration
Aldehydes (10)/Ketone (20)  Carboxylic Dehydration of 2-butanol to form 2 –
acids  CO2 butene OR 1-butene???
Primary alcohol  aldehydes  carboxylic Zaitsev’s rule states that in an elimination
acid reaction, the alkene with the greatest
 **Apply alcoholic drinking.. (Antidote?) number of alkyl groups on the double
 **Relate
Fetal Alcohol Syndrome For Women  bonded carbons (the more highly
Mental retardation, facial malformation, poor substituted alkene) is the major product
growth before and after birth of the reaction.
 Secondary alcohol  ketone
Tertiary alcohol  no reaction
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 LUCAS TEST
Lucas Reagent: Zinc chloride
 Esterification:
reaction between (catalyst) in concentrated HCl
carboxylic acid and alcohol (reactant)
Products: ester and water Involves double displacement
What is the reverse of esterification? Tertiaryalcohol are the MOST reactive
Why aspirin is NOT sold in liquid dosage towards this test
forms?
Primary alcohols do not undergo the
reaction easily >> needs heat
Visible result: two immiscible layers
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 THIOLS  PHENOLS
Aka mercaptans  hydroxyl group attached to an aromatic
ring
Nomenclature: same as alcohol
 The parent compound is also called
except the –ol suffix is replaced by –
_______, C6H5OH
thiol
 Properties
Eg: methanethiol, 2 butanethiol
 Form ion –dipole and hydrogen bonds
2,3-dimercaptopropanol (aka  Enhance water solubility
___________ or ___________)  Esterified to form prodrugs
Properties: foul odor, oxidized to  Susceptible to oxidation
disulfide.
Alliin  allicin Page 45 Page 46

 ETHERS
 Examples  Contain an -O- between two carbon groups
 Ortho (cathechol)  Simple ethers
named from -yl names of the
 Meta ( resorcinol) attached groups and adding ether.
 IUPAC: Use “oxy” + parent alkane name
 Para (hydroquinone)
 CH3-O-CH3
 1-napthol (alpha-naphthol)
 Derived:
 2-napthol (beta-naphthol)
 IUPAC:
 Eugenol
 CH3-O-CH2CH3
 Uroshiol
 Derived:

 IUPAC:
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Examples Anesthetics

 Diethyl ether
 Chloroform
 Cyclopropane

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 Classification
 Open-chain (Symmetric or asymmetric)
 Ring / Cyclic
 Examples
 Naproxen
 Ethylene oxide

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 Aldehydes and Ketones

The general formula for the saturated
homologous series of aldehydes and
ketones is CnH2nO.
THE CARBONYL GROUP AND
Aldehydes have at least ONE
CARBONYL-CONTAINING
HYDROGEN ATOM bonded to the
COMPOUNDS carbonyl group
Ketones have only alkyl or aryl
(denoted as Ar) GROUPS bonded to
the carbonyl group
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Nomenclature of Aldehydes
 ALDEHYDES:  IUPAC: Select longest continuous chain
 Oxidized to ________ and reduced to having the aldehyde group (aldehyde group
__________ is automatically C#1). Change –e of the
alkane name with –al.
 KETONES:
 eg.: CH3CH2CH2CHO
 Reduced to __________
 Common name: #C + aldehyde
 e.g: CH3CHO
 Derived name: Name of Alkyl group +
aldehyde
 e.g: CH3CH2CHO
 Examples of aldehydes: Vanillin, formaldehyde
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 TESTS FOR ALDEHYDES AND KETONES

Nomenclature of ketones
 Tollen’s test (___)
 IUPAC: Parent chain has the ketone group  basedon the ability of silver ions to oxidize
(given the lower number). Change –e to – ALDEHYDES;
one.  (+) result:
 Derived: Alkyl name + ketone  Fehling’s Test and Benedict’s Test
 Example:  theALDEHYDE group is oxidized to an acid by
Cu2+ ions.
CH3COCH3  Positive result: ________
 IUPAC Name:
 Derived Name: Ketones do NOT give positive test with Tollen’s, Fehling’s
 Use: and Benedict’s Tests therefore, these tests are used to
distinguish between aldehydes and ketones.
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Carboxylic Acid and Derivatives Classification of # OF

CARBON
NAME

 Contains _______ group Carboxylic acids 1 Form-

2 Acet-
 R-COOH  Saturated carboxylic acids 3 PROPION-
4 Butyr-
 Ar-COOH
/Monocarboxylic acid
5 Valeric acid
 Single bond, one carboxylic acid 6 Caproic acid
 Nomenclature: Enanthoic
 Unsaturated carboxylic 7
 IUPAC: Carboxyl group is ALWAYS C#1. Change –e acids/monobasic, monocarboxylic acid
to –oic acid. 8 Caprylic acid
acid Pelargonic
 Methane  methanoic acid 9
 Double bond/s, one carboxylic acid acid
 Common Name: Eg. Acetic acid, formic acid*  Examples: 10
12
 Use
of Greek prefixes (α - carbon next to COOH, β,  Linoleic acid (________)
14
Gamma, Epsilon)  Linolenic acid 16
 Arachidonic acid (found in animal fat) 18
20
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# OF
NAME STRUCTURE
CARBON
 Aromatic carboxylic acids 2 Oxalic acid HOOC-COOH
 Examples: benzoic acid; o-toluic acid; m- 3 Malonic acid
toluic acid; p-toluic acid 4 Succinic acid
5 Glutaric acid
 Dicarboxylic acids Adipic acid
6
 Two carboxyl groups 7 Pimelic acid
 Simplest dicarboxylic acid is ___. 8 Suberic acid
9 Azelaic acid
10 Sebacic acid
Remember this Mnemonic: Oh My Such
Good Apple Pie!
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CARBOXYLIC ACID DERIVATIVES

 Hydroxy acids  ESTERS

 Examples:  RCOOR

 Lactic acid  Nomenclature:

 salicylic
acid: Board Question: Component  IUPAC:
Use the alkyl or aryl portion of the alcohol
of Whitfield’s Ointment? name as the first name. Change –ic to –oate.
 tartaric acid  Ethanoic acid + methanol  methyl ethanoate
 Malic acid  Salicylic acid + methanol  _____

 Amino acids  Important reaction:

 Esterification:
 Examples: Essential Amino Acids:
 Hydrolysis: Reverse of esterification
 Characteristic: Pleasant odor. Upon
Page 63 hydrolysis, unpleasant Page 64

2. ANHYDRIDES
 Reaction between two carboxylic acids
 Anhydride : “without water”
 Example: Acetic anhydride ORGANIC NITROGEN
3. AMIDES COMPOUNDS: AMINES AND
R– CO – NH2 (carbonyl group bonded to
amine)
AMIDES
 Example: urea, penicillins

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AMINES
 Organic
compound that are derived from Alkaloids
ammonia
 PRIMARY

 SECONDARY
 Naturally occuring amines
 TERTIARY

 QUATERNARY – NOT basic, no lone pair of electron

present
 Examples:
 Aniline,
 Epinephrine,
 Atropine
 Nicotine
 Saccharin – artificial sweetener (Disadv: ___________)

AMIDES Page 67 Page 68

Amine Nomenclature

 Primary: alkanamimes
 Ethylamine, isopropylamine, cyclohexylamine
 Aromatic amines
 Aniline, metachloroaniline
 Secondary & Tertiary

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Nitrosamines

 Secondary amine + NaNO2 + HCl

 Potent carcinogens

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Amides

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STEREOCHEMISTRY

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 Chirality
 Isomers
 Chiralcarbon: four different substituents
attached to carbon atom Same molecular formula,
 Chiral carbon is optically _______ different in structure
 Optical Activity:
 Instrument: __________
 Rotations:
 Clockwise: _________
 Anticlockwise: __________
 Racemic

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 Stereoisomers – atoms are in the same order

Structural
Isomers – differ in order of but different orientation in space.
arrangement of the atoms or bond  Geometric Isomers

a] Chain Isomers  Cis-Trans Isomers

 Cis : same side
 Differ in the arrangement of C atoms
 Trans: opposite side
 (n-butane) and Isobutane
 Optical Isomers
b] Position Isomers  Enantiomer
 Differ in position of the substituent or  Non-superimposable MIRROR-IMAGE
unsaturated bonds (C=C, C =C)  Same physicochemical properties

 1-butene and 2-butene  D and L isomers

 Ex. D and L-glyceraldehyde
c] Functional Isomers
 Diastereomer
 Differ in their functional group  With at least 2 chiral centers, NOT MIRROR IMAGE, not super-
 Dimethyl ether and Ethanol imposable; different physico-chemical properties
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 Conformational Isomers or conformers Tautomerization

 Involves single bond only Tauto “same”; meros “part”
 Eg. CH3CH3 Special kind of isomerism
 Sawhorse representation Rapid interconversion between two
 Newman substances
 ball and stick model KETO-ENOL TAUTOMERS
Eg. Propanone to 2-propanol

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 What type of compound does each as

Sige Nga! follows belong?
 Muscone:

 Simplest alkane?  Citric acid:

 Undecylenic acid:
 Simplest alkene?
 Citral
 Simplest alcohol?
 Beta-carotene
 Simplest aldehyde?  Carbolic acid
 Simplest ketone?  Benzene

 Acetylene
 Simplestmonocarboxylic acid?
 Efficascent oil®
Dicarboxylic acid?
 Ethyl chloride

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 General Questions:
 Synonyms:
 Ilan ang asawa ni carbon? Type of bond?
 Alkane:
 Oxidation product of alcohol, USP?
 Alkene:
 Dietary precursor of prostaglandin?
 Alkyne:
 Isomers:
 Piatos na may itlog?  :Joke un?!
 Enantiomer
 Carbolic acid:
 Diastereomer
 Ant bites  Anomer

 Epimer

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 Functional Groups:  Functional Group Determination

 CnH2n+2 – RCOOR
 CH3OCH3
 CnH2n – RCOOH
 CH3CH2COOCH3
 CnH2n-2 – RNH2
 CH2CH2COCH3
– RX
 ROH
 CH3CH = CHCH2CH2OH
– Ar-OH
 ROR
– RSH
 RCHO
– R2NH
 RCOR

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