Chem 351 Ch 5: Chirality, Enantiomers, and Diastereomers

constitutional, diastereomers

____ isomers and ______ isomers must have different physical and chemical properties.

enantiomers

______ are configurational isomers that are mirror images of each other

diastereomers

______ are configurational isomers that are not mirror images of each other

enantiomers

______ are non superimposable mirror images of each other

enantiomers

______ can have identical properties depending on whether they are in a chiral or an achiral environment

achiral

______ compounds are said to be optically inactive

diastereomers

_______ are stereoisomers that are not mirror images of each other

racemic mixture

a _____ ____ contains equal amounts of the + and - enantiomers of a chiral molecule. The net result is zero rotation of the light.

stereocenter

a _____ is bonded to 4 different groups

racemic

a _____ mixture of enantiomers is optically inactive, despite being made up of chiral molecules

achiral

a meso molecule has 2 or more stereocenters but has a plane of symmetry making it _____

chiral

a molecule is ___ if it has an enantiomer

meso

a molecule is ____ if it contains at least two stereocenters but has a plane of symmetry making it achiral overall

achiral

a molecule is _____ if it does not have an enantiomer

enantiomer

a molecule is achiral if it does not have an _____

enantiomer

a molecule is chiral if it has an _____

achiral

a molecule that possesses a plane of symmetry must be _____

optically inactive

a racemic mixture of enantiomers is _____ _____ despite being made up of chiral molecules

optically inactive

achiral compounds are said to be _____ ____ because they leave the plane of polarization unchanged

chiral

any molecule that contains exactly one stereocenter must be _____

1

any molecule with exactly ___ stereocenter(s) must be chiral.

diastereomers

as long as they are different molecules, but not mirror images of each other, with the same molecular formula and the same connectivity, then they are ______

diastereomers

cis and trans alkenes are _____. They have the same molecular formula and the same connectivity, but they are different molecules and are not mirror images of each other.

diastereomers

cis and trans isomers with respect to a double bond are _____ of each other

stereoisomer

configurational isomers are a type of ____

clockwise

dextrorotatory compounds rotate light _____

different

diastereomers must have _____ physical and chemical properties

increases

double bond stability ______ as the amount of alkyl substitution increases

increases

double bond stability increases as the amount of alkyl substitution ______

R

double bonds become more stable as the number of attached ___ groups increases

optically active

enantiomerically pure chiral compounds are said to be _____ ____ because they rotate the plane of polarization

configurational

enantiomers and diastereomers are examples of _____ isomers

achiral

if a molecule and its mirror image rapidly interconvert, then the molecule is effectively _____

plane polarized

if all photons from a light source have their electric fields oscillating in the same plane, then the light is ____ ____

enantiomers

if two isomers are related by the inversion of all chiral centers, then the two molecules are ____

diastereomers

if two isomers are related by the inversion of some, but not all, chiral centers, then the two molecules are ______ of each other

enantiomers

if two molecules are nonsuperimposable and have opposite configurations at all three chiral centers, then they are _____

diastereomers

if two molecules have opposite configurations at two out of three chiral centers, then they are ______

chiral

in a _____ environment, enantiomers have different physical and chemical properties

different

in a chiral environment, enantiomers have ____ physical and chemical properties

same

in an achiral environment, enantiomers have the ____ physical and chemical properties

yes

is a nitrogen atom bonded to four different groups a stereocenter?

counterclockwise

levorotatory compounds rotate light ______

unpolarized

most light sources emit light that is ____. If we could view all the photons traveling in the same direction, we would see that each one's electric field oscillating in a different plane

vertical

on a fischer projection, the substituents on the _____ bonds are understood to point away from you

toward

on a fischer projection, the substituents on the horizontal bonds are understood to point _____ you

away

on a fischer projection, the substituents on the vertical bonds are understood to point ____

dextrorotatory

some chiral compounds rotate light clockwise in the + direction and are called _____

levorotatory

some chiral compounds rotate light counterclockwise in the - direction and are called _______

chiral

the body acts as a ____ environment

configurational

the max number of _____ isomers that can exist for a molecule with n chiral centers is 2^n

decreases

the stability of a carbon carbon double bond _____ when going from tetrasubstitued to monosubstituted

stereoisomers

to be _____, molecules must have the same molecular formula, be different molecules, and have the same connectivity

more

trans alkenes are _____ stable than cis alkenes

steric

trans isomers are more stable than cis isomers due to _____ strain

nitrogen inversion

uncharged nitrogen atoms that undergo _____ _____ are not stereocenters

asymmetric

when the stereocenter is a carbon atom, it's referred to as an _____ carbon

conformers, configurational

whereas ______ are related solely by rotations around single bonds, converting from one ______ isomer to another usually requires the breaking of a covalent bond and forming a new one