CEE 3 MODULE 1-ORGANIC CHEMISTRY

Organic chemistry

study of compounds containing carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, and phosphorus

Carbon

possesses 4 valence electron, can form hybrid orbitals, and can have multiple isomers

Catenation

ability to form multiple bonds with itself

Organic compound

made from one or more carbon and hydrogen atom

Hybridization

mixing of 2 or more nonequivalent atomic orbitals to form a new set of equivalent atomic orbitals

Sigma bond (σ bond)

head-on/end-to-end overlap; lies along the bond axis, accounts for the first bond, is the strongest, and can exist independently

Pi bond

Sideways or side-to-side overlap, which lies perpendicularly to the bond axis, accounts for the 2nd and 3rd bond, is the weakest, and cannot exist independently

tetrahedral, bent, trigonal pyramidal

geometry of sp3

trigonal planar

geometry of sp2

linear

geometry of sp

Kekule structure

Also known as line bond structure. Drawing of structures with the use of lines and dots

Lewis structure

electron dot or lewis dot structure. Use of dots to show bonds between atoms

Condensed structure

Single bonds are implied, and hydrogens of the same atom are combined. Double or triple bonds may be hidden. It uses parentheses for branched-out parts.

Skeletal structure

Bond-oine or line-angle structure. C-H or C-C atoms are not shown. And only non-carbon atomd are shown.

International Union of Pure Applied Chemistry

IUPAC means

London Dispersion/ Van der Waals

Forces present in all molecules and atoms

Dipole-Dipole

Polar molecules

Hydrogen bond

Molecules containing H bonded to F, O, or N

Resonance

Mesomerism principle of delocalization. Continuous motion (delocalization) of pi or lone electrons across consecutive sp2 carbon

Strains

Any unwanted disturbance/deviation from ideal bond angles

Ring strains

Due to Ring closure

Steric effect/Hindrance

Competition for space due to bulky group

Torsional strain

Due to small dihedral angles

Inductive effect

HIGH electronegative --> decrease stability

LOW electronegative --> increase stability

Stereochemistry

study of the spatial or 3D arrangement of atoms in a molecule

Isomerism

Compounds with the same chemical formula but different structures

Constitutional isomerism

Different connectivity of isomers

Stereoisomer

Orientation on the 3D space

Chain/skeletal isomer

Differ in the arrangement and branching of carbon

Positional isomer

differ in the arrangement or attachment of functional groups, substituent atoms, and multiple bonds

Functional isomer

differ in the functional group attached to them

Configurational isomer (optical isomer)

mostly based on chirality

Enantiomer

mirror image, but not superimposable

Diastereomers

non-superimposable non-mirror images

Meso compound

Mirror image and superimposable

Epimer

same in all position except for one carbon

D-mannose

Carbon 2 is the epimer of glucose

Allose

Carbon 3 epimer of glucose

D-galactose

Carbon 4 epimer of glucose

Anomer

only differ in the carbonyl carbon

Cis-trans isomer

Isomer with similar substituents

E/Z isomer

Isomer with different substituents

Cahn-ingold prelog rule

The geometric isomer follows what rule

Acyclic

uses solid, dash, wedge line in the structure

Solid line

along the plane

wedge line

to the front or towards the viewer

Dash line

to the back or away from the viewer

Anti-staggered

most stable acyclic conformation; the 2 largest groups are opposite of each other. 180 degrees away from each other.

gauche staggered

two largest groups are 60 degrees apart

partially eclipse

2 largest groups are 120 degrees away from each other

Eclipse

2 largest groups are 0 degrees away from each other

Chair

The most stable cyclic conformation

Addition

multiple reactant, 1 product

Elimination

One reactant, multiple product

Substitution

one of the substituents in a molecule is replaced to form new products

Rearrangement/isomerization

structure of the compound changes bonds or atoms to become an isomer of itself

Electrophile

Attacks atoms with a positive charge; electron-loving

Nucleophile

Attacks atoms with a negative charge; nucleus loving

Alkanes

free radical substitution

Alkene and alkynes

Electrophilic addition

Aromatics

Electrophilic aromatic substitution

Alkyl halide and alcohol

nucleophilic substitution

Carbonyl compound

nucleophilic addition

Carboxylic acid and derivatives

Nucleophilic acyl substitution

Aliphatic hydrocarbon

In chain form, and non-aromatic compounds

Paraffins

Alkanes; composed only of single bond

Olefins

Alkenes are composed of a double bond

Acetylene

Alkynes are composed of a triple bond

Alicyclic hydrocarbon

Cyclic/ring form, non-aromatic

Palladium

catalyst for hydrogenation/reduction involving alkenes

Vicinal dihalide

final product for halogenation involving alkenes

Markovnikov's rule

This rule defines that the major product is the most stable products

Linlard's catalyst

The catalyst used in hydrogenation/reduction involving reaction of alkynes

methylbenzene

other name of toluene

Methoxybenzene

Other name of anisole

Aminobenzene

Other name of Aniline

Sulfuric acid

Catalyst of nitration and sulfation for aromatic compound

Aluminum chloride

Catalyst used in Friedel-Craft alkylation

Potassium triiodide

Catalyst used in Frédéric-Craft acylation

Phenol, cresol

disinfectant

Hydroquinone

Astringent

Salicyclic acid

Keratolytic and anti-inflammatory

Aspirin

antithrombotic

Benzoic acid and benzoates

preservatives

Benzaldehyde

oil of bitter almonds

Alkyl halide

Comprises a halogen atom bonded to a saturated sp3-hybridized carbon atom

Alcohol

contains an alcohol group attached to a carbon chain

Methanol

toxin in adulterated alcohol

ethanol

essence of liquor and wine

Isopropyl alcohol

rubbing alcohol

ethylene glycol

anti-freeze; poison-->oxalic acid--> kidney failure

Octanol

for partition coefficient analysis

eugenol and thymol

phenolic volatile oil

Dimercaprol/BAL

antidote for Arsenic poisoning

Mercaptopurine

anticancer, antimetabolite

Propylthiouracil

antithyroid

N-acetylcysteine

mucolytic, antidote for paracetamol poisoning

Diethyl ether

oldest anesthetic

ethylene oxide

gas sterilizer

monobenzone

dipigmenting agent