orgo 4

Question 1

aromatic

Answer 1

stable and unreactive

Question 2

huckel’s criteria for aromaticity

Answer 2

1. Has to be a closed loop
2. Has to have 1 2p orbital unhybridized
3. P orbitals must overlap, the molecule must be planar
4. 4n+2 electrons in the closed loop, if there is 4n pi electrons then its called antiaromatic

Question 3

annulenes

Answer 3

cyclic hydrocarbons with single and double bonds; nomenclature [# carbons] annulene
[10] annulene- the Hs here cause repulsion forces into non-planar orientation so non-aromatic

Question 4

ortho

Answer 4

1,2

Question 5

meta

Answer 5

1,3

Question 6

para

Answer 6

1,4

Question 7

is phenol more acidic than alcohol? if so, why?

Answer 7

yes because resonance and charge delocalization

Question 8

electron donating group do what to pka

Answer 8

increases it, makes weaker acid, CH

Question 9

electron withdrawing group does what to pka

Answer 9

decreases it, stronger acid, O, Cl, F, N

Question 10

stronger effects where

Answer 10

ortho and para

Question 11

vinyl

Answer 11

2 carbons with a double bond

Question 12

allyl

Answer 12

2 carbons with a double bond

Question 13

radical stability

Answer 13

most substituted is more stable, methyl

Question 14

bromination is more _____ than chlorination

Answer 14

regioselective

Question 15

hammond’s postulate

Answer 15

The structure of the transition state is:

• Exothermic, transition state is reached early and resembles the reactants more than products
• Endothermic, transition state is reached later and resembles the products more

Question 16

an allylic hydrogen is ____ than a vinylic hydrogen because ___

Answer 16

weaker, resonance

Question 17

van der waals radius

Answer 17

intermolecular distance where the attractive and repulsive forces balance out

Question 18

haloalkanes are more or less dense than hydrocarbons alkanes

Answer 18

more

Question 19

C-X bonds are

Answer 19

polar

Question 20

C-H bonds are

Answer 20

nonpolar

Question 21

as you move down the PT from F, dipole moment

Answer 21

decreases

Question 22

halogens have higher or lower boiling points than hydrogen

Answer 22

higher bc theyre bigger

Question 23

nucleophile strength trend

Answer 23

X-> S> O >C > N

Question 24

leaving group strength trend

Answer 24

I>Br>Cl>H2O & neutrals> F>CH3COO- >OH- >NH2-

Question 25

favors SN1

Answer 25

Tertiary carbocation- carbocation stability
Better leaving groups
Large nucleophiles like I
Polar PROTIC solvents like water and alcohols

Question 26

favors SN2

Answer 26

Primary carbocation- access to reaction site
Linear shape
Small nucelophiles like Cl
Polar APROTIC solvents like DMSO, DMF and acetone

Question 27

aprotic increasing nucleophicity

Answer 27

I<br></br>

Question 28

protic increasing nucleophicity

Answer 28

F

Question 29

rate law for E1

Answer 29

FIRST ORDER, LG

Question 30

rate law E2

Answer 30

second order, 1st LG and 1st base