Organic Vocab

Question 1

Resonance structure

Answer 1

• don’t move atoms
• only move electrons
• keep track of formal charges (same net charge)
• make sure there are octets

Question 2

Importance of resonance structures

Answer 2

1) more octets and bonds
2) charges on compatably electronegative atoms
3) as little charge separation as possible
* don’t have any atoms with +/-2 charge

Question 3

Constitutional isomers

Answer 3

Aka structural isomers

Compounds w/ same formula, but different structures

Question 4

Stereoisomers

Answer 4

Aka geometric isomers
Isomers that have same connectivity but different special arrangement
Eg. cis/trans, E/Z, enantiomers, diasteriomers

Question 5

Lewis acids/bases

Answer 5

Electron acceptors/donators

Question 6

Factors affecting acidity

Answer 6

• Electronegativity-more electronegative means more acidic
• size of anions-bigger the atom, more acidic
• resonance stabilization
• inductive effects
• hybridization (sp»sp2>sp3)

Question 7

Inductive effects

Answer 7

Electrons are donated or withdrawn through the sigma bonds of a molc (spreads out e- density)
Helps stabilize carbocations

Question 8

Torsional/twisting strain

Answer 8

Destabilization caused by eclipsing bonds and repulsion between e-

Question 9

Steric strain/hinderance

Answer 9

Interference btwn 2 bulky groups that are too close to each other- e- clouds are too close and destabilize

Question 10

Reactivities of H’s in chlorination

Answer 10

Tirtiary: secondary: primary

5.5: 4.5: 1

Question 11

Reactivity of H’s in bromonation

Answer 11

Tertiary: secondary: primary

1600: 97: 1

Question 12

Hyperconjugation

Answer 12

Weak overlap of a sigma bond and p orbital (e- density in sigma bond is stabilized by being shared with p orbital)
Stabilizes cations

Question 13

Carbene

Answer 13

Neutral reactive intermediates containing a C with 2 atoms bound to it and 2 nonbonding e-

Question 14

Stereochemistry

Answer 14

Study of 3-D structure of molc

Question 15

Chirality

Answer 15

ability to exist in 2 non-superimposable mirror images

Question 16

Enantiomers

Answer 16

2 non-superimposable mirror images

Question 17

Diasteriomers

Answer 17

Stereoisomers that aren’t mirror images

Question 18

Chiral center

Answer 18

An atom that is not superimposable on its mirror image

Question 19

Stereocenter

Answer 19

An atom at which the interchange of 2 groups gives a stereoisomer

Question 20

Chiral carbon

Answer 20

A C with 4 different groups attached to it

Question 21

How many stereoisomers can something have?

Answer 21

2^n (n=chiral center)

Question 22

Absolute configuration

Answer 22

Description of the spatial arrangement of the groups attached to a chiral center (R/S)
Uses Cahn-Ingold-Prelog Priority system

Question 23

Optically active

Answer 23

A molecule that can rotate polarized light

Question 24

Meso compound

Answer 24

Achiral compound with chiral centers