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Organic Chemistry 2 > Exam 2 > Flashcards

Exam 2 Flashcards

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1
Q

How much more stable are conjugated dienes than isolated dienes?

** Because of resonance!!! **

A

Conjugated dienes are 27 kJ/mol more stable than isolated dienes

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2
Q

Examples of EWG

A

Aldehydes, Ketones, Esters, Amides, Carboxylic Acids, Nitriles, Nitros, Sulfones, & Sulfoxides

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3
Q

Examples of EDG

A

Alkoxys, Syllyloxys, Aminos, Ester’s oxygen, Amide’s nitrogen, Alkyls

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4
Q

Diene Reactivity

A

** Want most stable s-cis conformation **

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5
Q

Diels-Alder Reaction Stereochemistry

A

Concerted mechanism = no changes in conformation

** Racemic mixtures because products are not chiral, so products must not have chirality **

Endo Transition State: EWG pointing in towards newly formed pi bond

** Stabilized by overlap between pi bond and p-orbital **

Exo Transition State: EWG pointing away from newly forming pi bond

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6
Q

Pyrrole

A

Resonance Energy = 22 Kcal/mol

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7
Q

Imidazole

A
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8
Q

Furan

A

RE = 16 Kcal/mol

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9
Q

Thiophene

A

RE = 29 Kcal/mol

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10
Q

Pyridine

A

RE = 22 Kcal/mol

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11
Q

Pyrimidine

A
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12
Q

Purine

A
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13
Q

Indole

A
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14
Q

Benzofuran

A
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15
Q

Quinoline

A
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16
Q

Benzene

A

RE = 36 Kcal/mol

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17
Q

Napthalene

A

RE = 60 Kcal/mol total, 30 Kcal/mol per ring

** Resonance energy per ring decreases as conjugation increases **

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18
Q

Anthracene

A

RE = 84 Kcal/mol total, 28 Kcal/mol per ring

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19
Q

Phenanthrene

A

RE = 91 Kcal/mol total, 30 Kcal/mol per ring

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20
Q

Phenol

A
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21
Q

Toluene

A
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22
Q

Xylene

A
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23
Q

Aniline

A
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24
Q

Benzoic Acid

A
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25
Q

Styrene

A
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26
Q

Anisole

A
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27
Q

Cresol

A
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28
Q

Aromatic Ring

Common Nomenclature

A

Name substituents with ortho (o), meta (m), para (p)

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29
Q

Aromatic Ring

IUPAC Nomenclature

A

Number the substituents with their position number

30
Q

EAS

A

Electrophilic Aromatic Substitution

Aromatic Ring = Nucleophile

Carbocation = Electrophile

** Look for absence of leaving group and strong Nucleophile **

31
Q

Chlorination

A

Reagents: Cl2 / AlCl3

Active Electrophile: Cl-Cl+ - AlCl3

32
Q

Bromination

A

Reagents: Br2 / FeBr3

Active Electrophile: Br-Br+-FeBr3

33
Q

Iodination

A

Reagents: 1/2 I2 / HNO3

Active Electrophile: I+

34
Q

Nitration

A

Reagents: HNO3 / H2SO4

Active Electrophile: O=N+=O

35
Q

Sulfonation

A

Reagents: SO3 / H2SO4

Active Electrophile: +SO4H

36
Q

Desulfonation

A

Reagents: H30+ / H2O / Δ

37
Q

Where do EDGs direct?

A

Ortho & Para

25x more reactive than benzene

Increases reaction rate

38
Q

What’s different about Anisole compared to toluene?

A

Anisole is 1000x more reactive than benzene because it has a resonance structure with all octects filled (4 instead of 3 res. structures)

39
Q

Where do EWGs direct?

A

Meta

** Avoids placing the carbocation next to the partial positive from the EWG **

Decelerates reaction rates

40
Q

EDGs Directing Strength

(Most to Least)

A
  • NH2
  • OH
  • OCH3
  • NHCOCH3

Alkyl / -CH3

-H

41
Q

Halides’s Directing Ability

A

Mildy Deactivating while Directing O/P

  • F
  • Cl
  • Br
  • I
42
Q

EWGs Directing Strength

(Most to Least)

A

Strongly Deactivating and Directs Meta

  • CHO
  • CO2H
  • OCCH3
  • SO3H
  • CN
  • NO2
  • +NR3
43
Q

What is unique about halides as directing groups?

A

They are EDGs, but because they’re:

Inductively deactivating (less polar bond)

+ Resonancely mildly activating (poor p-orbital overlap)

= Mild Deactivating while directing to O/P

44
Q

What is special about aniline and phenoxide?

A

Their by-products are more reactive than the original molecule, so they undergo overhalogenation and while substitube at all O/P positions

Aniline = needs buffer (NaHCO3)

Phenoxide = needs buffer (NaOH)

45
Q

Kobe-Schmitt Reaction

A

Importance: Commercial production of aspirin

Reagents: 1) NaOH / CO2, 2) HCl

Extra step for aspirin: 3) CCOOOCC (turns OH into -OR)

** Need to already have a hydroxy (-OH) group / phenoxide **

46
Q

Friedel-Craft Alkylation

A

Adds alkyl group to aromatic ring

Reagents: Carbocation + Aromatic Ring

47
Q

Carbocation Formation from a Halide

A

Reagents: AgNO3 / Δ OR AlCl3

** Rearrangment can occur **

48
Q

Carbocation Formation from Alcohol

A

Reagents: H2SO4 OR H3PO4 OR BF3

** Rearrangment can occur **

49
Q

Carbocation Formation from Alkene

A

Reagents: H2SO4 OR H3PO4

** Rearrangment can occur **

50
Q

3 Limitations of FC Alkylation

A
  1. No FC Alkylation on strongly deactivated rings (halides okay)
  2. Beware of carbocation rearrangment
  3. Potential for over alkylation w/EDGs
51
Q

Acyl Group

A

-COR

52
Q

Formyl Group

A

Fm

53
Q

Acetyl group

A

Ac

54
Q

Benzoyl Group

A

Bz

55
Q

How to name acyl group (IUPAC)

A

Name R group on acyl group, then change the ending to -oyl

ex: butane -> butanoyl

56
Q

Friedel-Craft Acylation

A

Adds acyl groups to aromatic rings

Reagents: Acid chloride/anhydride, AlCl3, + aromatic ring

57
Q

Gatterman-Koch Formylation

A

Adds formyl group to aromatic ring

Reagents: CO / HCl / AlCl3 / CuCl

58
Q

How does FC Acylation compare to Alkylation?

A
  1. No reaction on strongly deactivated rings
  2. No carbocation rearrangments
  3. No over acylation possible (acyl groups deactivate aromatic rings)
59
Q

How do you do alkylation without the carbocation rearrangment?

A

Do an acylation, then use a clemmensen reduction to get rid of the C=O

Clemmensen Reducation Reagents: Zn(Hg) / HCL

60
Q

NAS

A

Nucleophilic Aromatic Substitution

Two Mechanisms: Addition-Elimination & Benzyne

61
Q

Addition-Elimination NAS Mechanism

A

Conditions: Leaving group on aromatic ring, EWG at the O and/or P positions

Reagents: Aromatic Ring (electrophile) + Nucleophile

X = F, Cl, Br, I, OTs

62
Q

Benzyne NAS Mechanism

A

Conditions: Leaving group on aromatic ring with no EWG at O/P positions

Reagents: Aromatic ring w/EDG groups + Nucleophile

** Many products possible at each β-hydrogen can be attacked two ways **

63
Q

Dissolving Metal Reduction

A

NH3 + Naº ⇔ NH3•e- + Na

64
Q

Birch Reduction

A

Reagents: Na OR Li / NH3(l) / ROH

EWG: Sandwiched by the double bonds

EDG: In conjugation with double bonds

** Mechanism involving radicals **

65
Q

Copper Coupling

A

Reagents: R’-X + R2CuLi

R’-X + R2CuLi → R’-R

66
Q

Heck Reaction

A

Reagents: Pd+2 / PPh3 / TEA

“Who the heck peed twice in my tea”

Molecules: R-X + C=C-R’ → R-C=C-R’

67
Q

Suzuki Reaction

A

Reagents: Pdº / NaOH

“Suzuki bike (B) with handlebars (OH2)

68
Q

Williamson Ether Synthesis

A

Reagents: NaOEt

69
Q

Oxidation

A

Reagents: warm, conc. Na2Cr2O7 / H2SO4

Turns everything but quatenary carbon centers on branches, esters, methoxys, and carboxylic acids into carboxylic acid branches

70
Q

Oxidizing Phenol

A

Turns phenol into quinone

Organic Chemistry 2 (4 decks)

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