Term
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Definition
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Term
| the reason for handedness in molecules: |
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Definition
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Term
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Definition
| molecules that contain no plane of symmetry and are not superimposeable on their mirror-images |
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Term
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Definition
| a C bonded to 4 different groups |
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Term
| some groups that can't be chirality centers |
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Definition
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Term
| optically active substances |
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Definition
| substances that, when in solution, rotate the plane of plane-polarized light |
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Term
| the angle of rotation of optically active substances can be measured with... |
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Definition
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Term
| some things about a substance's rotation that can be measured |
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Definition
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Term
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Definition
| a compound whose solution rotates plane-polarized light to the right |
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Term
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Definition
| a compound whose solution rotates plane-polarized light to the left |
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Term
| the extent of rotation depends on... |
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Definition
-concentration
-path length
-wave length |
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Term
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Definition
| the optical rotation of a chiral compound under standard conditions, such as concentration of 1g/mL, sample path length of 1 dm, and light of wavelength 589 nm |
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Term
| rules for assigning configurations at a chirality center |
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Definition
1: assign priorites to each group bonded to the C by using Cahn-Ingold-Prelog rules
2: orient the molecule so that the group of lowest priority is pointing to the rear
3: draw a curved arrow from group 1 to group 2 to group 3
4: if the arrow rotates clockwise, the chirality center is R, and if the arrow rotates counterclockwise, the chirality center is S |
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Term
| how to assign priorites to each group bonded to the C by using Cahn-Ingold-Prelog rules |
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Definition
1: rank each atom by atomic number (atoms with higher atomic numbers get higher priorities)
2: if a decision can't be reached based on the first atom, look at a second or third atom until a difference is found
3: multiple bonded atoms are equivalent to the same number as single bonded atoms |
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Term
| is the sign of optical rotation related to R, S designation? |
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Definition
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Term
| how R, S designations have been proven to be correct |
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Definition
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Term
| a molecule with 2 chirality centers can have how many possible stereoisomers? |
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Definition
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Term
| depiction of the relationship between enantiomers and diastereoisomers |
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Definition
| photograph figure 5-10 on p. 131 |
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Term
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Definition
| stereoisomers that are not mirror images |
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Term
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Definition
| diastereoisomers whose configuration differs at only 1 chirality center |
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Term
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Definition
| occurs when a compound with 2 chirality centers possesses a plane of symmetry |
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Term
| a meso compound is ______ despite having 2 chirality centers |
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Definition
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Term
| a meso compound is achiral despite ______ |
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Definition
| having 2 chirality centers |
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Term
| racemic mixture (racemate) |
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Definition
| a 50:50 mixture of 2 enantiomers |
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Term
| the optical rotation of racemic mixtures |
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Definition
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Term
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Definition
| differ in connections between atoms |
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Term
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Definition
| have different C skeletons |
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Term
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Definition
| contain different functional groups |
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Term
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Definition
| have functional groups in different positions |
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Term
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Definition
| have the same connections between atoms, but different geometry |
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Term
| types of diastereoisomers |
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Definition
-configurational diastereoisomers
-cis-trans isomers |
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Term
| how cis-trans isomers differ |
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Definition
| they differ in the arrangement of substituents on a ring or a double bond |
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Term
| other elements that can be chirality centers |
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Definition
| other elements wit tetrahedral atoms |
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Term
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Definition
| able to be converted from achiral to chiral in a single chemical step |
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Term
| how to identify prochirality for a sp2 hybridized C |
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Definition
| 1: draw the plane that includes the atoms bonded to that sp2 C
2: assign priorities to the groups bonded to that C
3: draw a curved arrow from group 1 to group 2 to group 3
4: the face of the plane on which the curved arrow rotates clockwise is the Re face
5: the face on which the arrow rotates counterclockwise is the Si face |
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Term
| when an atom that is sp3 hybridized has a prochirality center |
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Definition
| when it becomes a chirality center after one of its attached groups is replaced |
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Term
| how to identify prochirality in an sp3 hybridized atom |
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Definition
| 1: for CH2X, imagine a replacement of 1 H with deuterium
2: rank the groups, including deuterium
3: if the replacement leads to R chirality, the atom is pro-R
4: if the replacement leads to S chirality, the atom is pro-S |
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Term
| when a C is not a stereocenter |
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Definition
| when it has 2 of the same group attached to it |
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Term
| how to determine whether the stereocenter has the R or S configuration |
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Definition
1: give each of the 4 groups a number (1-4)
2: use the orientation of these numbers to determine the configuration |
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Term
| how to assign numbers to the groups around a stereocenter |
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Definition
1: make a list of the 4 atoms attached to the stereocenter
2: rank those atoms based on atomic number |
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Term
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Definition
| compound that has an internal plane of symmetry |
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Term
| when compounds are chiral |
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Definition
| when they have stereocenters and they and are not meso |
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Term
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Definition
| compound makes plane polarized light rotate clockwise |
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Term
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Definition
| compound makes plane polarized light rotate counterclockwise |
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Term
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Definition
rotates polarized light clockwise
given a minus (+) sign |
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Term
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Definition
rotates polarized light counterclockwise
given a minus (-) sign |
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Term
| the number of stereoisomers a molecule with chirality centers can have |
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Definition
| 2n stereoisomers, where n = # of chirality centers |
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Term
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Definition
| atom whose replacement leads to an R chirality |
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Term
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Definition
| atom whose replacement leads to an S chirality |
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Term
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Definition
| the face on which the arrows curve clockwise |
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Term
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Definition
| the face on which the arrows curve counterclockwise |
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