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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
Styrene
26
Anisole
27
Cresol
28
Aromatic Ring Common Nomenclature
Name substituents with ortho (o), meta (m), para (p)
29
Aromatic Ring IUPAC Nomenclature
Number the substituents with their position number
30
EAS
Electrophilic Aromatic Substitution Aromatic Ring = Nucleophile Carbocation = Electrophile \*\* Look for absence of leaving group and strong Nucleophile \*\*
31
Chlorination
Reagents: Cl2 / AlCl3 Active Electrophile: Cl-Cl+ - AlCl3
32
Bromination
Reagents: Br2 / FeBr3 Active Electrophile: Br-Br+-FeBr3
33
Iodination
Reagents: 1/2 I2 / HNO3 Active Electrophile: I+
34
Nitration
Reagents: HNO3 / H2SO4 Active Electrophile: O=N+=O
35
Sulfonation
Reagents: SO3 / H2SO4 Active Electrophile: +SO4H
36
Desulfonation
Reagents: H30+ / H2O / Δ
37
Where do EDGs direct?
Ortho & Para 25x more reactive than benzene Increases reaction rate
38
What's different about Anisole compared to toluene?
Anisole is 1000x more reactive than benzene because it has a resonance structure with all octects filled (4 instead of 3 res. structures)
39
Where do EWGs direct?
Meta \*\* Avoids placing the carbocation next to the partial positive from the EWG \*\* Decelerates reaction rates
40
EDGs Directing Strength | (Most to Least)
- NH2 - OH - OCH3 - NHCOCH3 Alkyl / -CH3 -H
41
Halides's Directing Ability
Mildy Deactivating while Directing O/P - F - Cl - Br - I
42
EWGs Directing Strength | (Most to Least)
Strongly Deactivating and Directs Meta - CHO - CO2H - OCCH3 - SO3H - CN - NO2 - +NR3
43
What is unique about halides as directing groups?
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
What is special about aniline and phenoxide?
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
Kobe-Schmitt Reaction
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
Friedel-Craft Alkylation
Adds alkyl group to aromatic ring Reagents: Carbocation + Aromatic Ring
47
Carbocation Formation from a Halide
Reagents: AgNO3 / Δ OR AlCl3 \*\* Rearrangment can occur \*\*
48
Carbocation Formation from Alcohol
Reagents: H2SO4 OR H3PO4 OR BF3 \*\* Rearrangment can occur \*\*
49
Carbocation Formation from Alkene
Reagents: H2SO4 OR H3PO4 \*\* Rearrangment can occur \*\*
50
3 Limitations of FC Alkylation
1. No FC Alkylation on strongly deactivated rings (halides okay) 2. Beware of carbocation rearrangment 3. Potential for over alkylation w/EDGs
51
Acyl Group
-COR
52
Formyl Group
Fm
53
Acetyl group
Ac
54
Benzoyl Group
Bz
55
How to name acyl group (IUPAC)
Name R group on acyl group, then change the ending to -oyl ex: butane -\> butanoyl
56
Friedel-Craft Acylation
Adds acyl groups to aromatic rings Reagents: Acid chloride/anhydride, AlCl3, + aromatic ring
57
Gatterman-Koch Formylation
Adds formyl group to aromatic ring Reagents: CO / HCl / AlCl3 / CuCl
58
How does FC Acylation compare to Alkylation?
1. No reaction on strongly deactivated rings 2. No carbocation rearrangments 3. No over acylation possible (acyl groups deactivate aromatic rings)
59
How do you do alkylation without the carbocation rearrangment?
Do an acylation, then use a clemmensen reduction to get rid of the C=O Clemmensen Reducation Reagents: Zn(Hg) / HCL
60
NAS
Nucleophilic Aromatic Substitution Two Mechanisms: Addition-Elimination & Benzyne
61
Addition-Elimination NAS Mechanism
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
Benzyne NAS Mechanism
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
Dissolving Metal Reduction
NH3 + Naº ⇔ NH3•e- + Na
64
Birch Reduction
Reagents: Na OR Li / NH3(l) / ROH EWG: Sandwiched by the double bonds EDG: In conjugation with double bonds \*\* Mechanism involving radicals \*\*
65
Copper Coupling
Reagents: R'-X + R2CuLi R'-X + R2CuLi → R'-R
66
Heck Reaction
Reagents: Pd+2 / PPh3 / TEA "Who the heck peed twice in my tea" Molecules: R-X + C=C-R' → R-C=C-R'
67
Suzuki Reaction
Reagents: Pdº / NaOH "Suzuki bike (B) with handlebars (OH2)
68
Williamson Ether Synthesis
Reagents: NaOEt
69
Oxidation
Reagents: warm, conc. Na2Cr2O7 / H2SO4 Turns everything but quatenary carbon centers on branches, esters, methoxys, and carboxylic acids into carboxylic acid branches
70
Oxidizing Phenol
Turns phenol into quinone

Organic Chemistry 2 (4 decks)

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