Organic Chemistry 2 Test

Front 1

What's the structure of a methyl Alkyl Halide?

Back 1

SP3 hybridized Carbon bonded to 3 Hydrogens and one Halogen (X)

Front 2

What's the structure of a primary Alkyl Halide?

Back 2

SP3 hybridized Carbon bonded to 1 R group, 2 Hydrogen, 1 Halogen (X)

Front 3

What's the structure of a secondary Alkyl Halide?

Back 3

SP3 hybridized Carbon, 2 R groups, 1 Hydrogen, 1 Halogen (X)

Front 4

What's the structure of a tertiary Alkyl Halide?

Back 4

SP3 hybridized Carbon, 1 Halogen (X), 3 R groups

Front 5

What is the structure of an Allylic Halide?

Back 5

CH2CH2C-X (Chain of 3 Carbon, double bond between first two)

Front 6

What is the general equation of a nucleophilic substitution reaction?

Back 6

R--X + Nu- ----> R--Nu + X-

Front 7

Define the leaving group in a nucleophilic substitution reaction

Back 7

Typically Halogen, that breaks a bond with the carbon and keeps the electrons, typically forming a negatively charged species.

Front 8

Characteristics of a Good Leaving group

Back 8

Halogen, weak base with strong conj. acid, more stable with the negative charge (so neutral when attached to C)

Front 9

Periodic trend of leaving group ability

Back 9

Ability increases across a row and down a column

Front 10

Rank the compounds in order of worse to better leaving group ability:

HO-, H2N-, F-, H3C-

Back 10

H3C-<H2N-<OH-<F-

Front 11

Characteristics of a good nucleophile

Back 11

Strong base, wants to attack an electrophile to share electrons/donate e- pair

*affected by steric effects and solvent effects

Front 12

General periodic trend of nucleophilicity

Back 12

decreases across a row and up a column

(opposite trend of Leaving Group ability)

Front 13

Is water a better nucleophile or leaving group? Why?

Back 13

Leaving group, when attached to a carbon, it has a positive charge, wants electrons.

Front 14

What is steric hinderance in nucleophilicity?

Back 14

When there are bulkier groups on the nucleophile, it is worse at bonding to the C--X group.

Front 15

Example of a sterically hindered Nucleophile

Back 15

t-buOK (tert-butoxide) has too make CH3 groups on it to be able to attack the structure

Front 16

What are solvent effects?

Back 16

Depending on if the solvent is protic or aprotic, nucleophile trends are affected

Front 17

Protic solvent, examples, effects on periodic trend of nucleophile

Back 17

Can form Hydrogen bonds (contains O-H or N-H bonds), examples are: Water, MeOH, EtOH, CH3COOH, tBuOH. Nucleophilicity increases with size of the ion.

Front 18

Example of aprotic solvents

Back 18

Acetone, THF, DMF, DMSO