L2: Organic Chemistry: A Review

Organic Chemistry

Organic Chemistry

the study of compounds that contain the element carbon.

Organic Chemicals

affect virtually every facet of our lives.

octet

A carbon atom can reach an ______ of electrons in various ways

four

A carbon atom can bond to ______ other atoms

1. Carbon

2. Hydrogen

3. Oxygen

4. Nitrogen

5. Phosphorus

6. Sulfur

Elements in our body.

Silicon

__________can also be a basis of organic matter

organic compounds

Vast majority of over 20 million known compounds are based on C: ___________

C and H

Organic compounds generally contain __________ and other elements

Isomers

have identical composition but different structures

• Structural isomers

• Stereoisomerism

Two forms of isomerism

Structural

Species with the same elemental composition but the atoms are linked together in different ways

Structural

Same formula, different structure

Structural Isomers

Ether

the oxygen is in the middle. - COC

Stereoisomerism

Same atom-to-atom connections but different orientation in space

Stereoisomerism

Could only exist between 2 molecules

Geometric isomers

occur in molecules containing a C=C double bond.

Geometric isomers

Cis

faces the same side

Trans

arrange at the opposite ends (up;down)

Trans fat

unsaturated fatty acids.

Optical isomers

______________ are molecules that are non-superimposable mirror images.

hands

ex. of Optical isomers

chiral

Molecules with this quality (optical isomers) are termed “_______”.

enantiomers

Pairs of non-superimposable, mirror-image molecules

Enantiomers

non-super imposable

Lactic acid isomers are _______________________.

Chiral

____________ pairs rotate plane polarized light in equal but opposite directions. (Left and Right)

Chirality

generally occurs when a central carbon atom has four unique groups attached.

Carbon compounds

are notable for their resistance to chemical change

STRONG BONDS And Slow Reactions

Carbon compounds are notable for their resistance to chemical change due to ___________ and ______________

Carbon compounds

non-highly reactive

Hydrocarbons

compounds of C and H

Hydrocarbons

often a third or more additional elements

• Alkanes

• Alkenes

• Alkynes

• Cycloalkanes

• Aromatic

Subgroups of Hydrocarbons

Alkanes

Containing only C-C single bonds

Alkenes

C=C double bonds as well as single bonds

Alkynes

carbon-carbon triple bonds as well as single bonds

Cycloalkanes

tetrahedral carbon atoms joined in a ring

Aromatic

hydrocarbons containing benzene rings

CnH2n+2

Alkanes have the general formula _______________

Alkanes

are “saturated” hydrocarbons, or saturated with hydrogens

Alkanes

Only single bonds

Alkanes

Alkanes

are colorless gases, liquids, and solids

Alkanes

Low reactivity, however they easily undergo combustion

Alkanes

Non-polar (or low polarity), low solubility in water

Alkanes

Exist mostly as gasses and liquids

Hexagon

one of the most stable shapes; could be easily maintained; strong enough to be maintained.

International Union of Pure and Applied Chemistry

IUPAC stands for

IUPAC system

The _______________ of nomenclature provides a system of naming organic compounds.

IUPAC system

Using the ________________, each organic compound gets a unique and unambiguous name.

Systematic

The IUPAC name—e.g., 2-[4-(2-methylpropyl)phenyl]propanoic acid

Generic

The official, internationally approved name of the drug—e.g., ibuprofen

Trade

The name assigned by the company that manufactures the drug—e.g., Motrin or Advil

Cycloalkanes

Rotation about single bonds allow molecules to adopt the lowest energy conformation

Cyclohexane

___________________, C6H12, has interconverting “chair” and “boat” forms.

CnH2n

Cycloalkanes formula

Alkenes

names end in “-ene”

CnH2n

General formula for alkene with one double bond is _____________

alkenes

the root of the name is determined by the longest carbon chain that contains the double bond

Alkenes

The position of the double bond is indicated with a number, and when appropriate, the prefix, cis or trans is added.

Geometric Isomers

Result of loss of free rotation about the C=C brings about “_______________”

Alkenes

Increase in reactivity over alkanes

Alkenes

X-Y addition reactions are possible

Alkenes

X2, H2, HX and H2O can add across the double bond

Alkenes

are said to be “unsaturated” since the carbon atoms have less than 4 sigma bonds

Alkenes

Molecules such as Br2, H2, HCl, HBr, and H2O add across the double bond.

hydrogenated

Fats can be “_____________” with H2

partially hydrogenated

Peanut butter has _______________vegetable oil.

Alkenes

unsaturated; fluid

Alkynes

have carbon-carbon triple bonds.

C2H2

Alkyne formula

acetylene

ethyne

C2H2:

common name =

systematic name =

1,1,2,2-tetrachloroethane

The addition of 2 mol of chlorine to ethyne (acetylene) gives _________________

Benzene

___________, C6H6, is a key molecule in chemistry

Benzene

C6H6

Benzene

It is the simplest aromatic compound

Benzene

a class of compounds so named because they have significant, and usually not unpleasant, odors.

Benzene; C6H6

_________ has two resonance structures with alternating double bonds.

delocalized

Resonance in Benzene

The pie/3.14 electrons are ________ over the ring.

True

Toluene – NOT an IUPAC name

T/F

Naphthalene

2 benzenes combined together (alcampor)

Substitution Reactions

Reactions of Aromatics

alcohol

If one of the hydrogen atoms of an alkane is replaced by a hydroxyl (O-H) group, the result is an ___________

alcohol

ROH

Methanol and ethanol

are the most important alcohols

Ethanol

___________ is a primary alcohol.

Ethanol

It is oxidized to an aldehyde and then on to an acid

Alcohols

__________ are a derivative of water

true

Many alcohols dissolve in water

T/F

Glycols

_________: Alcohols with Two –OH Groups

antifreeze

Ethylene glycol aka “____________”

Glycerol Alcohol

_____________ with 3 OH Groups

Ethers

have the general formula R-O-R

diethyl ether

The best known ether

ethers

Lacking an R-OH group, the properties of ________ are in sharp contrast to those of alcohols.

amines

are derivatives of NH3

amines

Generally have terrible odors

bases

Amines, like NH3, are ____________