Exam 2

Question 1

Reactivity of carboxylic acid family least to greatest

Answer 1

carboxylic acid, amide, ester, anhydride, acid chloride

Question 2

Stability of carboxylic acid family from least to greatest

Answer 2

acid chloride, anhydride, ester, amide, carboxylic acid

Question 3

Basicity of amines

Answer 3

1. less resonance = more basic
2. Presence of an EWG = less basic
3. More basic = more nucleophilic
4. More p character = better base

Question 4

Aldehydes are more reactive than ketones because of

Answer 4

sterics and hyperconjugation

Question 5

Primary alcohol + PCC

Answer 5

Aldehyde

Question 6

Secondary alcohol + PCC/H2CrO4

Answer 6

Ketone

Question 7

Alkene + O3 and Me2S

Answer 7

2 ketones (ozonolysis)

Question 8

Carbonyl + strong nucleophile

Answer 8

addition of nucleophile first

Question 9

Carbonyl + weak nucleophile

Answer 9

protonation first

Question 10

LiAlH4 is more reactive than NaBH4 because

Answer 10

Aluminum is less electronegative than Boron, so the Al-H bond is easier to break

Question 11

Ketone + LiAlH4/NaBH4 and H3O+

Answer 11

Secondary alcohol

Question 12

Aldehyde + LiAlH4/NaBH4 and H3O+

Answer 12

Primary alcohol

Question 13

R-Br + Mg

Answer 13

R-MgBr (Grignard)

Question 14

Ketone/Aldehyde + ylide (R’-(-)CH-(+)PPh3)

Answer 14

Replace O with H-C-R’

Question 15

Alkyl halide + PPh3 + strong base

Answer 15

ylide formation

Question 16

Ketone + H2O

Answer 16

1,1-diol

Question 17

Ketone + R’OH

Answer 17

Carbonyl O becomes 2 OR’ (after reacting twice)

Question 18

Ketone + R’NH2

Answer 18

Carbonyl O becomes N-R’ (after reacting twice, imine)

Question 19

Cat HA examples

Answer 19

Sulfuric acid, toluene sulfonic acid, and methane sulfonic acid

Question 20

Cyclic hemi-acetals

Answer 20

-stable hemiacetals in 5 or 6 membered rings
-can be reacted with HA to break the ring
-alcohol and aldehyde on either side of a 5 or 6 membered chain reacted with HA forms a hemiacetal

Question 21

Protonated amines are more stable and less reactive than unprotonated amines because

Answer 21

They no longer have a lone pair to react with

Question 22

Benzene ring with Cl attached + NaNH2 and liquid NH3

Answer 22

Cl substituent becomes NH2

Question 23

NO2 + Fe and HCl

Answer 23

NO2 becomes NH2

Question 24

Aldehyde + NH2OH and HA followed by NaBH4

Answer 24

primary amine

Question 25

Imine + NaBH4/LiAlH4

Answer 25

attach H to N

Question 26

NH2 + Acid chloride and pyridine

Answer 26

attach ketone to N

Question 27

Acid chloride + excess NH3

Answer 27

replace Cl with NH2

Question 28

Carboxylic acid + H2O

Answer 28

Conjugate base of carboxylic acid and H3O+

Question 29

Carboxylic acid + R'OH and cat HA

Answer 29

Remove H from OH on carboxylic acid and replace with R'

Question 30

Carboxylic acid + CH2N2

Answer 30

Remove H from carboxylic acid and replace with a methyl

Question 31

Acid chloride + R'NH2

Answer 31

Replace OH from carboxylic acid and replace with NHR'

Question 32

Acid chloride + carboxylic acid

Answer 32

remove H from carboxylic acid and Cl from acid chloride and join the two structures

Question 33

Acid chloride + ROH

Answer 33

Replace Cl with OR

Question 34

Carboxylic acid + NaBH4/LiAlH4

Answer 34

Primary alcohol