O Chem: Ch 4: Stereochemistry

Enantiomers

non superimposable mirror image stereoisomer

Stereoisomer

(cis and trans) have some connectivity, but differ in their arrangement space

Nonsuperimposable

molecules cannot be placed on top of each other and give the same molecule

Structural isomers

same molecular formula, but differ in connectivity

Diastereomers

stereoisomers that are not enantiomers

Meso compounds

have chiral atoms, but are achiral due to a plane of symmetry or an inversion center

Diastereomers can only be separated by what?

normal chromatography

Enantiomers can be separated by what?

resolution

Racemic mixtures

equal quantities of R and S enantiomers (only chiral)

Greek word for "handed

chiral

When molecule and mirror image are identical?

achiral

A C atoms with 4 different groups bonded to it is considered what?

stereogenic

What is the # of alkyl groups attached to double bonds?

degree of substitution

What states that there is an absence of molecules with double bonds at the bridgehead position?

Bredt's rule

Terminal alkynes are strong what donors?

proton (acidic behavior)

What is a material that increases the rate of the reaction without being consumed?

catalyst

What is the construction of target molecules from smaller pieces?

synthesis

What are interconvertible through rotations around a bond within a molecule?

conformational isomers

What are molecules with the same formula, but different connectivities?

constitutional isomers

What is thalidomide now used for?

cancer therapy and anti-leprosy agent

For the heats of formation of hexenes, the more substituted the double bond is, what?

the more stable the molecule is

Is cis or trans more stable?

trans

For properties of simple alkenes, the more Carbons it has, the what?

more stable it is

If the melting point is higher, then the intermolecular forces are what?

stronger

What is the general method for separating the constituent enantiomers of a racemic mixture?

resolution

Acidity of alkynes deals with what?

percent s character

Flow Chart: Given A and B, if they don't have the same molecular formula, what does that mean?

they are not isomers

Flow Chart: Given A and B, if they have the same molecular formula, but the connections aren't to the same atoms, they are what?

constitutional isomers

Flow Chart: Given A and B, if they have the same molecular formula, and the connections are all to the same atoms, and A and B ARE superimposable, what does that mean?

A and B are identical, might be meso compounds

Flow Chart: Given A and B, if they have the same molecular formula, and the connections are all to the same atoms, and A and B are NOT superimposable, they could be what?

mirror images

Flow Chart: Given A and B, if they have the same molecular formula, and the connections are all to the same atoms, and A and B are NOT superimposable, and they ARE mirror images, what does this mean?

A and B are enantiomers

Flow Chart: Given A and B, if they have the same molecular formula, and the connections are all to the same atoms, and A and B are NOT superimposable, and they ARE NOT mirror images, what does this mean?

A and B are diastereomers