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Chapter 5
Organic Chemistry- Exam 2
| Question | Answer |
|---|---|
| What are isomers? | Different compounds that have the same molecular formula. |
| What are stereoisomers? | Compounds with the same connectivity but different 3-D arrangements |
| When can cis/trans notation be used for alkenes? | When there is a like group on each alkene carbon. |
| Why can't C=C bonds freely rotate? | Maintaining π-bond orbital overlap prevents free rotation. |
| What is a chiral object? | An object that is not identical to its mirror image. |
| What does superimposable mean? | Two objects can be placed over one another so all parts coincide. |
| What commonly creates chirality at carbon? | A carbon bonded to four unique groups. |
| What is a chirality center? | A tetrahedral atom attached to four different groups. |
| What are enantiomers? | Stereoisomers that are non-superimposable mirror images |
| Can an achiral compound have an enantiomer? | No. |
| How can an enantiomer often be drawn from a chiral structure? | Invert the dashes and wedges at the chirality center(s). |
| What do enantiomers have at corresponding chirality centers? | Opposite configurations. |
| What system assigns R or S configuration? | The Cahn–Ingold–Prelog (CIP) system. |
| How is CIP priority assigned? | Higher atomic number gets higher priority. |
| What should you do with the lowest-priority group when assigning R/S? | Orient it away from you. |
| What does clockwise 1→2→3 indicate? | R configuration. |
| What does counterclockwise 1→2→3 indicate? | S configuration. |
| How are tied priorities resolved in CIP? | Compare atoms one layer at a time until the first point of difference. |
| How are double bonds treated for CIP comparison? | As if the bonded atom is attached to two equivalent atoms. |
| What happens if two groups on a chirality center are switched? | The configuration becomes the opposite configuration. |
| What do R and S describe? | The configuration at a chirality center. |
| What do (+) and (−) describe? | The direction of optical rotation. |
| Is there a direct correlation between R/S and (+)/(−)? | No |
| What does optically active mean? | Able to rotate plane-polarized light. |
| What is a racemic mixture? | A 50/50 mixture of two enantiomers. |
| What is the optical rotation of a racemic mixture? | 0°, because the rotations cancel. |
| What are diastereomers? | Stereoisomers that are not mirror images. |
| How do diastereomers differ from enantiomers in physical properties? | Diastereomers have different physical properties. |
| What is the maximum number of stereoisomers for n chirality centers? | 2^n, before accounting for symmetry/meso compounds. |
| Can a molecule with multiple chirality centers be achiral? | Yes, if it has an appropriate plane of symmetry. |
| What is a meso compound? | A compound with chirality centers that is achiral because of symmetry. |
| What does a plane of symmetry imply? | The molecule is achiral. |
| What do horizontal lines represent in a Fischer projection? | Attachments coming out of the page. |
| What do vertical lines represent in a Fischer projection? | Attachments going back into the page. |
| How may a Fischer projection be rotated without changing the molecule? | Only 180° in the plane; do not flip it. |
| When is E/Z notation used for alkenes? | When the alkene substituents make cis/trans inadequate. |
| How are E/Z priorities assigned? | Prioritize the groups attached to each alkene carbon by atomic number. |
| When is an alkene Z? | The highest-priority groups are on the same side. |
| When is an alkene E? | The highest-priority groups are on opposite sides |