Organic Chemistry

Alkane

Alkene

Alkyne

Ketone

Aldehyde

carboxylic acid

Ester

Acid Halide

PEroxy acid

Amide

• Carboxcylic Acid
• Anhydride

Primary Amine

Secondary Amine

Tertiary Amine

Alcohol

Ether

• Thiol
• mercaptan

Benzene

Benzyl

Phenyl

• Peroxide
• technically hydrogen peroxide

Epoxide

Carbonmate

Ketal

Acetal

• Thiol ether
• sulfide

Results from a transfer of electrons

results from sharing of electrons

a region of space where an electron is likely to be found

only two electrons can occupy any atomic orbital, and to do so these two must have opposite spins.  These electrons in opposite spins are said to be paired.

• Linear
• 0 lone pairs
• 180 degree bond angle

OR

3 lone pairs

OR 

4 lone pairs

• Trigonal Planar
• 0 lone pairs
• 120 degree bond angle

• Tetrahedral
• 0 lone pairs
• 109 degree bond angle

• Trigonal Bipyramid
• 0 lone pairs
• 120 degree bond angle on horizontal plane
• 90 degree bond angle on vertical plane

• Octahedral
• 0 lone pairs
• 90 degree bond angle

• Bent or angular
• 1 lone pairs
• 120 degree bond angle

OR

• 2 lone pairs
• 109 degree bond angle

• Trigonal Pyramid
• 1 lone pairs
• 109 degree bond angle

• Sawhorse or SeeSaw
• 1 lone pairs
• 120 degree bond angle on horizontal plane
• 90 degree bond angle on vertical plane

• Square Pyramid
• 1 lone pairs
• 90 degree bond angle

• T Shape
• 2 lone pairs
• 90 degree bond angle

OR 

3 lone pairs

• Square Planar
• 2 lone pairs
• 90 degree bond angle

One end of the bond is relatively negative and the other end is relatively positive (i.e. there is a negative pole and a positive pole).

Alcohol

Thiol

Sulfide

Sulfide

Nitro

Ketone

Nitrile

Ether

Ester

Disulfide

Acid Chloride

Alkane

Alkyne

Amine

Alkene

Carboxylic Acid

Imine

Arene

Alkyl Halide

Anhydride

Amide

reduces ketones to alkanes with NH2OH then KOH

R2CuLi + RCOCl (creates ketones from chlorides)

Negatively charged atom

Positively charged atom

The distance between two bonded atoms

The amount of energy needed to split bonded atoms

Compounds with just carbon and hydrogen atoms

Molecules with the same kinds and numbers of atoms in different structural orders

-ene

-ol

-one

-ate

when two non-identical atoms are bonded, they must have different electronegativities, and will attract the shared electrons to different extents, creating a dipole

the outermost (most loosely held) electrons

a region of zero electron density separating regions of opposite sign in an orbital.

• When it’s used: for short chain alkanes and alcohols.
• What it means: n- means “normal” –  an unbranched chain with the functional group (if present) on the 1-position. s- means “secondary”, t- means “tert“.
• Why it’s useful: Just a shorthand way of describing different structural isomers.
• Notes: n-hexane is another frequently encountered name, which simply represents a linear six-carbon chain. “Hexanes”, which you might see in the lab, refers to a mixture of different (branched) isomers of hexane.(it’s purified by distillation, and the isomers have very similar boiling points, so it’s sold as “hexanes”. Pure n-hexane is more expensive because separating it from its isomers is a royal pain).

• When it’s used: for amines and amides.
• What it means: The N- signifies that the substitutent is connected to the nitrogen.Example: N-methyl butylamine, N,N-dimethylformamide.
• Why it’s useful: it removes ambiguity. “Methyl butylamine”, for instance, could refer to an isomer where the methyl group is on the carbon chain.
• Notes; when different substituents are present on the nitrogen, the terminology is N-(substituent),N-(substituent), for instance N-methyl,N-ethylbutylamine.

• When it’s used: for sugars and amino acids.
• What it means: It goes back to Emil Fischer, who designated the two enantiomers of glyceraldehyde (the simplest sugar) L-glyceraldehyde and D-glyceraldehyde. At a time (1890) where techniques for determining absolute structure were not available,  he GUESSED(!) that structure of the leveratory (left-rotating) and dextrarotatory (right-rotating) structures of glyceraldehyde was as depicted in the Fischer projection, and gave them the prefixes L and D respectively. Thankfully, when X-ray crystallography was developed, it was found that his guess was correct.   In L-sugars, the oxygen on the  carbon second from the end is on the left hand side in the Fischer projection. In D-sugars, the oxygen is on the right-hand side.
• Why it’s useful: It was originally used to correlate the absolute structures of sugars to the two glyceraldehydes. It is no longer useful for this purpose, but like the appendix, it hangs around anyway. Like the  appendix, it only seems to get noticed when it causes problems.
• Notes: This notation causes a lot of confusion. Just because something is “D” does not mean it rotates polarized light to the right and vice versa [that is the function of (+)- and (–)]. For example D-fructose rotates polarized light to the left (–). Furthermore, any correlation between L/D and S/R is coincidental. The 20 essential amino acids in the body are L-amino acids. They are all (S) except for cysteine, which is (R) (due to the sulfur having higher priority in the Cahn-Ingold-Prelog rules). Racemates are written as DL (for instance, DL-glucose is the racemic mixture).

methane

ethane

propane

butane

pentane

hexane

heptane

octane

nonane

decane

a carbon atom that is bonded to four different groups

structures that differ only by rotations about single bonds. in most cases, conformers interconvert at room temperature; thus, they are not different compounds and not true isomers

stereoisomers that are not mirror images

a pair of nonsuperimposable mirror image molecules: mirror image isomers

a plane of symmetry through the middle of a molecule, dividing the molecule in to two mirror image halves. a molecule containing this plane cannot be chiral.

Washing the product of unwanted impurities

• used to separate solvents based on their relative densities
• the denser solvent is always drained first

• transfer of a dissolved compound from a starting solvent into a solvent in which the product is more soluble
• like dissolves like
• use separatory funnel

• isolates solid from liquid using paper filter
• solid is the residue
• liquid is the filtrate
• 2 types: gravity and vacuum filtration

• solvent's own weight pulls it through the filter
• solvent is desired product
• use hot solvent

• solvent forced through filter by a vacuum
• solid is desired product
• use Buchner flask

an isomer having the higher-priority groups on the same side of the double bond

an isomer having the higher-priority groups on opposite sides of the double bond

a compound with two carbon-carbon double bonds

a compound with three carbon-carbon double bonds

a compound with four carbon-carbon double bonds

you can never determine exactly where an electron is, can only approximate

when there are two or more unfilled orbitals electron will go in different ones

Flourine

stronger

stronger

species with available electrons to make a bond

species that can accept a pair of electrons to make a bond

electrophile

nucleophile

any species that can donate a proton

any species that can accept a proton

a reaction in which two groups add to opposite faces of the double bond

a reaction in which two groups add to the same face of a double bond

when a proton acid adds to the double bond of an alkene, the proton bonds to the carbon atom that already has the most hydrogen atoms. in an electrophilic addition to an alkene, the electrophile adds in such a way that generates the most stable intermediate

Gas

Liquid

Solid

4

It must have some double or triple bonds and thus is not bonded to as many hydrogens as possible

It has only single bonds and is bonded to as many hydrogens as possible.

The possession by two or more distinct compounds of the same molecular formula, each molecule having the same number of atoms of each element, but in different arrangement

The existence of an element in two or distinct forms; diamond and graphite

Meta

Ortho

Para

Where the double Oxygen bond is placed

No, they have different numbers of hydrogens

ketone

Vinegar

Aldehyde

an ion with both + and - charges in same ion

the elimination of a molecule of water from an alcohol. OH is removed from one carbon and H is removed from the other

the intermolecular force in which a hydrogen atom that is bonded to a highly electronegative atom is attracted to an unshared pair of electrons of an electronegative atom in a nearby molecule

any of a class of alcohols having 2 hydroxyl groups in each molecule

any of a class of alcohols having 3 hydroxyl groups in each molecule

phenyl, aryl

Aniline

Benzene

Benzoic Acid

Toluene

Nitrobenzene

Phenol

Halogenation

Nitration

Sulfonation

Alkylation

Acylation

Oxidation

Reduction of Substituent to Single Bonds

Reduction of Ring and Substituent to Single Bonds

Reduction to Alkyl

Reduction to Aniline