Organic Chemistry Exam 1 Rutgers

Urea

(NH2)2CO

Equation used by Friedrich Wohler

NH4(OCN) -> NH3 + HOCN -> (NH2)2CO

Ammonia Cyanate

NH4(OCN)

Octet Rule

C, N, O, F atoms attain stable configurations when they have eight electrons in their outer shell

Methane

CH4

Ethane

C2H6 (Single Bond)

Ethylene

C2H4 (Double Bond)

Acetylene

C2H2 (Triple Bond)

Nitrogen

3 Bonds

Ammonia

NH3

Aminomethane

CH3NH2

Acetonitrile

CH3CN

Oxygen

2 Bonds

Water

H2O

Methanol

CH3OH

Formadehyde

H2CO

Halogen

(F,Cl,Br,I) 1 Bond

Chloromethane

CH3Cl

bromoethene

C2H3Br

Hydrogen

1 Bond

Neopentane

C5H12

Positive Formal Charger

One more bond than normal (loss e-)

Negative Formal Charge

One less bond than normal (GAIN e-)

Charged Carbon Atoms

3 bonds

Electronegativity

• Measure how electron density is distributed in covalent bonds. (Tendency to attract atoms to make covalent bonds)

Polarity

Molecules having uneven distribution of charges

partial charges and dipole moment

Partial charge

S+ and S-, covalent bond goes towards S-

Emphasis on character of atom

More electronegative atom is more negative

Dipole moment

Arrow, emphasis on character of bond

Polarizability (Atomic radii)

The weakening attraction between the nucleus and ins outermost electrons as an atom becomes larger

Polarizability trend

Increases down and to the left

Bond Length

Distance between to atoms in a covalent bond.

Vary dependent on Bond order and Atom identity

Bond length trend

Higher bond order = Shorter length

More electronegative = Shorter length

Resonance

A phenomenon that occurs when two objects naturally vibrate at the same frequency. Only electrons move for resonance

Quantum Number

n = 1,2,3,4

Angular Momentum Quantum Number

(l) indicates the shape of the orbital

n - 1

Magnetic Quantum Number

ml (-l to l)

Spin Quantum number

-Ms

+1/2 or -1/2

Pauli Exclusion Rule

two e- sharing an orbital MUST have opposite spins

Hund's Rule

e- fill in single first THEN in pairs to minimize electron-electron repulsion in an atom's orbitals.

Aufbau Principle

An electron occupies the lowest-energy orbital that can receive it n+0.7(l) FIRST (ie. 1s)

Valance Electrons

Electrons in the outermost shell

Inner Shell/Core Electrons

Electrons in lower numbered shells than valance

sp

Linear, 2 electron pairs, 180*

sp2

Trigonal Planer, 3 electron pairs, 120*

sp3

Tetrahedral, 4 electron pairs, 109.5*

Sigma bonds

Single covalent bond

Pi bonds

• Additional bonds after a single bond

• double (1)

• triple bond (2)

Solid wedge line

Line projects out of the plane of a page

Dashed Lines

Line recedes being the plane of the page

Methyl Carbocation

CH3+

Methyl Carbanion

CH3-

Methyl Radical

CH3

Methylene Carbene

CH2

Order for naming Molecules

1. Substituents, 2. Compound Root, 3. Multiple-bond index, 4. Principle Functional Group

Names of Alkanes Order

1. Methane, 2. Ethane, 3. Propane, 4. Butane, 5. Pentane, 6. Hexane, 7. Heptane, 8. Octane, 9. Nonane, 10. Decane

Cyclo- Prefix

Ring

-ane

Only Single bonds

-ene

One Double bond

-yne

One Triple Bond

-diene

Two double bonds

1. Carboxylic Acid

-COOH

2. Sulfonic Acid

-SO3H

3. Ester

-COO-

4. Acid Chloride

-COCl

5. Amide

-CONH2

6. Nitrile

-CN

7. Aldehyde

-CHO

8. Ketone

-CO-

9. Alcohol or Phenol

-OH

10. Thiol

-SH

11. Amine

-NH2

12. Alkene

Double Bond

13. Alkyne

Tripe Bond

14. Ether

-O-

15. Benzene

6 Carbons with 3 double bonds

Alkyl-

-R

Alkoxy-

-OR

Acetyl-

-COCH3

Amino-

-NH2

Bromo-

-Br

Carboxy-

-COOH

Chloro-

-Cl

Cyano-

-C Triple bond N

Fluoro-

-F

Formyl-

-COH

Hydroxy-

-OH

Iodo-

-I

Nitro-

-NO2

Mercapto

-SH

Oxo-

=O

Phenoxy-

-O-Benzene

Electronegativity trend

INCREASE: up and to the right

Sulfur (S)

6 ve-

Phosphorus (P)

5 ve-

Carbon (C)

4 ve-

Boron (B)

3ve-

Potassium (K)

1 ve-

Sodium (Na)

1ve-

Beryllium (Be)

2ve-

Magnisum (Mg)

2ve-