Mechanisms and Structures

Question 1

Where can mechanism arrows start from?

Answer 1

ONLY
(1) bond
(2) LP
(3) unpaired e- (radical)
- CHARGE NOT AN OPTION

Question 2

When is a compound more acidic?

Answer 2

When its conjugate base is more stable

Question 3

Sample reasoning for a compound being the most acidic form a list

Answer 3

BLANK is the most acidic because its conjugate base (what is it?) has resonance to share between the BLANK and BLANK, which is more stabilizing than the SECOND COMPOUND’s conjugate base resonance, which is being share between BLANK AND BLANK

Question 4

Acidity Rules

Answer 4

SERHI
Size (applies if atom has H or charge)
Electronegativity
Resonance (more S character = more acidic)
Inductive effect (more EN atoms nearby = more acidic)

Question 5

When is a lone pair more stable?

Answer 5

When it is closer to nucleus &/or has more s character

Question 6

Nucleophilic Acyl Substitution

Answer 6

(1) Nucleophile forms bond w/ carbonyl carbon of acyl group
(2) Carbonyl carbon breaks bond w/ leaving group

Question 7

Carbonyl carbon

Answer 7

C=O

Question 8

Acyl Group

Answer 8

C attached to carbonyl C

Question 9

Strong Base-Catalyzed Ester Hydrolysis

Answer 9

(1) nucleophilic addition
(2) elimination of OR’
(3) deprotonation of carboxylic acid

Question 10

Ester

Answer 10

O=C-O

Question 11

When is SN1 fastest? When is SN2 fastest?

Answer 11

SN1: fastest w/ methyl halides & primary alkyl halides
SN2: fastest w/ tertiary alkyl halides

Question 12

Methyl Halide

Answer 12

CH3 + halide

Question 13

Alkyl Halides

Answer 13

Hydrcarbon w/ halogen(s)

Question 14

Does SN1 have carbocation intermediate? SN2?

Answer 14

SN1: yes
SN2: no

Question 15

What happens when SN1 is attacked? SN2?

Answer 15

SN1: scrambling
SN2: inversion

Question 16

In what solvent is SN1 sped up? SN2?

Answer 16

SN1: polar protic
SN2: polar aproptic

Question 17

Polar Protic vs. Polar Aprotic

Answer 17

Polar protic: OH or NH; can form H bonds; highly polar
Polar aprotic: group solvents; medium range of polarity but polar bc of polar bonds (such as C=O)

Question 18

Rate of SN1? SN2?

Answer 18

SN1: rate = k [alkyl halide]
SN2: rate = k [nucleophile][alkyl halide]

Question 19

What should you include when drawing orbital diagrams?

Answer 19

Degrees