Organic Chemistry

Fall, 2011 by Dr.Isam Al Naser

Credits: 2 hours Class schedule : San (11-13,30) section1., Tus (11-13,30)section2 Class room:6038 Room number: 7234 Office hours: Mon (09-12) Wed (09-11), (13-15)

Lecture & Assignment Schedule (NEW)

Week 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Date 29-03/10 06-10/10 13-17./10 20-24/10 27-31/10 03-07/11 10-14/11 17-21/11 24-28/11 01-05/12 08-12/12 15-19/12 22-26/12 29-02/13 05-09/13 12-23/13 Topics to be covered Introduction to the Study of Organic Chemistry Introduction to the Study of Organic Chemistry Polar covalent bonds Alkanes and their stereochemistry Radical, Reaction of Alkanes Cycloalkanes and ther stereochemistry
Alkenes :structure and reactivity

Exams

Mid Exa
Alkenes: reactions and synthesis Alkynes stereochemistrys reactions of alky halides reactions of alky halides Alcohols and phenols Ethers and Epoxides Final Exa

Mid Exa

Final Exa

Text Book
Organic Chemistry 7th Edition, (Brooks/Cole Publishing Company) 2008 by
Authors John Mc Murry ISBN :978-1-4080-2052-4

Grading
Quizzes in class: 15% Exam :
35%

Final exam
50%

Chapter 1 Structure & Bonding

Organic chemistry is the study of the compounds of carbon.

Includes biological molecules, drugs, solvents, dyes,food additivives,pesticides.. Does not include metal salts and materials (inorganic)

Organic chemistry ,study of carbon compounds why is carbon special?

-90% of more than 30 million chemical compounds contain carbon. -Examination of carbon in periodic table answers some of these questions. -Carbon is group 4A element, it can share 4 valence electrons and form 4 covalent bonds.

1.1 Atomic Structure

Atom:

(2x10-10 m) 10-14 ~ 10-15 m 10-10 m

Nucleus
Protons (+) neutrons

Shell: A region of space around a nucleuses Where electrons are found. Orbital: A region of space where an electron or pair of electron,spend90-95%fo time. 2 10-10 m Diameter (200 picometers (pm)) [the unit angstrom () is 10-10 m = 100 pm]

Electrons (-)

Atomic Number and Atomic Mass

The atomic number (Z) is the number of protons in the atom's nucleus H=1,C=6,P=15 The mass number (A) is the number of protons plus neutrons H=1,008 C=12,011 P=30,974 Isotopes are atoms with the same atomic number but different mass numbers ,that have different numbers of neutrons

Shapes of Atomic Orbitals for Electrons

Four different kinds of orbitals for electrons based on those derived for a hydrogen atom Denoted s, p, d, and f s and p orbitals most important in organic and biological chemistry s orbitals: spherical, nucleus at center p orbitals: dumbbell-shaped, nucleus at middle d orbitals: elongated dumbbell-shaped, nucleus at center

Orbitals and Shells

part 1

Orbitals are grouped in shells of increasing size and energy Different shells contain different numbers and kinds of orbitals Each orbital can be occupied by two electrons

1.2 Electron Configuration of Atoms

Ground-state electron configuration

Rules 1-3 at page 4

See Table 1.1 as examples

1.3 Chemical Bonding Theory

2D to 3D

Tetrahedral carbon atom

1.4 The Nature of Chemical Bonds

Ionic Bonds

Bond between ions due to the electrostatic attraction : NaCl

Covalent Bonds
Bonds formed by sharing electrons Lewis structures (electron-dot) Nonbonding electrons (lone-pair electrons)

1.4 The Nature of Chemical Bonds

Lewis structures

Number of covalent bonds

1.4 The Nature of Chemical Bonds

Kekul

strutures (line-bond structure)

Table 1.2

1.5 The Nature of Chemical Bonds: Valence Bond Theory

Covalent bond forms when two atoms approach each other closely so that a singly occupied orbital on one atom overlaps a singly occupied orbital on the other atom -Two models to describe covalent bonding. Valence bond theory, Molecular orbital theory

Valence Bond Theory: Electrons are paired in the overlapping orbitals and are attracted to nuclei of both atoms HH bond results from the overlap of two singly occupied hydrogen 1s orbitals H-H bond is cylindrically symmetrical, sigma (s) bond

Bond Energy

Reaction 2 H H2 releases 436 kJ/mol Product has 436 kJ/mol less energy than two atoms: HH has bond strength of 436 kJ/mol. (1 kJ = 0.2390 kcal; 1 kcal = 4.184 kJ)

Bond Length

Distance between

nuclei that leads to maximum stability If too close, they repel because both are positively charged If too far apart, bonding is weak

1.5 Forming Covalent Bonds

Valence Bond Theory

Overlapping of two atomic orbital.

Bond strength
energy

Bond length
distance

1.5 Forming Covalent Bonds

Molecular orbitals (MO)

There are two ways for the orbital combination to occur-an additive way and a subtractive way . The additive way leds to formation of a MO that is lower in energy and roughly egg-shaped . The subtractive way leads to formation of a MO has a specific size, MO that is higher in shape and energy exa.H2 energy and has a node between nuclei

1.6 Hybridization sp3 Orbitals and the Structure of Methane

Carbon has 4 valence electrons (2s2 2p2) In CH4, all CH bonds are identical (tetrahedral) sp3 hybrid orbitals: s orbital and three p orbitals combine to form four equivalent, unsymmetrical, tetrahedral orbitals (sppp = sp3), Pauling (1931)

The Structure of Methane

sp3 orbitals on C overlap with 1s orbitals on 4 H atoms to form four identical C-H bonds Each CH bond has a strength of 436 (438) kJ/mol and length of 109 pm Bond angle: each HCH is 109.5, the tetrahedral angle.

Ethane:
CH3-CH3

Two Cs bond to each other by s overlap of an sp3 orbital from each Three sp3 orbitals on each C overlap with H 1s orbitals to form six CH bonds CH bond strength in ethane 423 kJ/mol CC bond is 154 pm long and strength is 376 kJ/mol All bond angles of ethane are tetrahedral

1.8 Double and Triple Bonds

1.8 sp2 Orbitals and the Structure Ethylene

Ethylene of C2H4 s bond P bond

sp2 hybrid orbitals: 2s orbital combines with two 2p orbitals, giving 3 orbitals (spp = sp2). This results in a double bond. sp2 orbitals are in a plane with120 angles Remaining p orbital is perpendicular to the plane

Structure of Ethylene

H atoms form s bonds with four sp2 orbitals HCH and HCC bond angles of about 120 CC double bond in ethylene shorter and stronger than single bond in ethane Ethylene C=C bond length 134 pm (CC 154 pm)

1.9 sp Orbitals and the Structure of Acetylene

C2H2 One s-bond & two pbonds

C-C a triple bond sharing six electrons Carbon 2s orbital hybridizes with a single p orbital giving two sp hybrids two p orbitals remain unchanged sp orbitals are linear, 180 apart on x-axis Two p orbitals are perpendicular on the y-axis and the z-axis

Orbitals of Acetylene

Two sp hybrid orbitals from each C form spsp s bond pz orbitals from each C form a pzpz p bond by sideways overlap and py orbitals overlap similarly

Bonding in Acetylene

Sharing of six electrons forms C C Two sp orbitals form s bonds with hydrogens

1.10 Hybridization of Nitrogen and Oxygen

Elements other than C can have hybridized orbitals HNH bond angle in ammonia (NH3) 107.1 C-N-H bond angle is 110.3 Ns orbitals (sppp) hybridize to form four sp3 orbitals One sp3 orbital is occupied by two nonbonding electrons, and other three sp3 orbitals have one electron each, forming bonds to H and CH3.

1.12 Drawing Structures

Drawing every bond in organic molecule can become tedious. Several shorthand methods have been developed to write structures. Condensed structures dont have C-H or C-C single bonds shown.. e.g.

33

Different compounds having the same molecular formula are called isomers When the group of atoms that make up the molecules of different isomers are bonded together in fundamentally different ways, we refer to such compounds as constitutional isomers. There are seven constitutional isomers of C4H10O, and structural formulas for these are drawn in the following table. There are no double or triple bonds and no rings in any of these structures.. Note that each of the carbon atoms is bonded to four other atoms, and is saturated with bonding partners.

Structural Formulas for C4H10O Isomers Kekul Formula Condensed Formula Shorthand Formula