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Organic Chemistry II > Exam 2 > Flashcards

Exam 2 Flashcards

1
Q

Reactivity of carboxylic acid family least to greatest

A

carboxylic acid, amide, ester, anhydride, acid chloride

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2
Q

Stability of carboxylic acid family from least to greatest

A

acid chloride, anhydride, ester, amide, carboxylic acid

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3
Q

Basicity of amines

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

Aldehydes are more reactive than ketones because of

A

sterics and hyperconjugation

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5
Q

Primary alcohol + PCC

A

Aldehyde

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6
Q

Secondary alcohol + PCC/H2CrO4

A

Ketone

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7
Q

Alkene + O3 and Me2S

A

2 ketones (ozonolysis)

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8
Q

Carbonyl + strong nucleophile

A

addition of nucleophile first

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9
Q

Carbonyl + weak nucleophile

A

protonation first

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10
Q

LiAlH4 is more reactive than NaBH4 because

A

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

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11
Q

Ketone + LiAlH4/NaBH4 and H3O+

A

Secondary alcohol

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12
Q

Aldehyde + LiAlH4/NaBH4 and H3O+

A

Primary alcohol

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13
Q

R-Br + Mg

A

R-MgBr (Grignard)

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14
Q

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

A

Replace O with H-C-R’

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15
Q

Alkyl halide + PPh3 + strong base

A

ylide formation

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16
Q

Ketone + H2O

17
Q

Ketone + R’OH

A

Carbonyl O becomes 2 OR’ (after reacting twice)

18
Q

Ketone + R’NH2

A

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

19
Q

Cat HA examples

A

Sulfuric acid, toluene sulfonic acid, and methane sulfonic acid

20
Q

Cyclic hemi-acetals

A

-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

21
Q

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

A

They no longer have a lone pair to react with

22
Q

Benzene ring with Cl attached + NaNH2 and liquid NH3

A

Cl substituent becomes NH2

23
Q

NO2 + Fe and HCl

A

NO2 becomes NH2

24
Q

Aldehyde + NH2OH and HA followed by NaBH4

A

primary amine

25
Q

Imine + NaBH4/LiAlH4

A

attach H to N

26
Q

NH2 + Acid chloride and pyridine

A

attach ketone to N

27
Q

Acid chloride + excess NH3

A

replace Cl with NH2

28
Q

Carboxylic acid + H2O

A

Conjugate base of carboxylic acid and H3O+

29
Q

Carboxylic acid + R’OH and cat HA

A

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

30
Q

Carboxylic acid + CH2N2

A

Remove H from carboxylic acid and replace with a methyl

31
Q

Acid chloride + R’NH2

A

Replace OH from carboxylic acid and replace with NHR’

32
Q

Acid chloride + carboxylic acid

A

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

33
Q

Acid chloride + ROH

A

Replace Cl with OR

34
Q

Carboxylic acid + NaBH4/LiAlH4

A

Primary alcohol

Organic Chemistry II (2 decks)

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