ORGANIC CHEM

List the order of priority of IUPAC groups

1. Carboxylic Acid

2. Ester

3. Acid Halide

4. Amide

5. Nitrile (CN)

6. Aldehyde

7. Ketone

8. Alcohol

9. Phenol

10. Amine

11. Alkene

12. Alkyne

13. Alkane

14. Ether

15. Alkyl Halide

16. Nitro (NO)

“Crazy Exes Always Act Nasty After Kissing At Parties And After-hours, Everyone Acts Naughty.”

pH < pka

protonate

pH = pka

protonate

pH > pka

deprotonate

Do SN1s and E1’s have rearrangements

Yes

Do SN2s and E2’s have rearrangements

No

Does SN2’s have inversions?

Yes

Does SN1’s have inversions?

No (± major/minor)

Does E2 care about sterochem?

Yes (Anti)

Does E1 care about sterochem?

No

Name 3 things about activating groups (e- density, EDG/EWG, o/p/m)

• increasing e- density

• EDG

• o/p

Name 3 things about deactivating groups (e- density, EDG/EWG, o/p/m)

• decreasing e- density

• EWG

  • -F, -Cl, -Br, -I (deactivators)

• m

Which 4 reagents do Michael (1,4) Addition?

• CN

• HNR₂

• R₂CuLI

• HSR

Which 4 reagents do Direct (1,2) Addition?

• NaBH₄

• LiAlH₄

• -MgX

• -Li

What is the hybridization of pi bonds in ethene?

2p-2p

What is the hybridization of sigma bonds in ethene?

sp²-sp²

What is the hybridization of the C-H bonds in ethene?

1s-sp²

Which is more acidic, EDG or EWG?

EWG > EDG

Oxymercuration-Demurcuration

Ozonolysis (Reducing Conditions)

Ozonolysis (Oxidizing Conditions)

Friedel-Crafts Alkylation

Friedel-Crafts Acylation

Wolff-Kishner Reduction

Clemmenson Reduction

Oxidative Cleavage

Williamson Ether

Self-Aldol Condensation

Mixed Aldol Condensation

Self-Claisen Condensation

Mixed-Claisen Condensation

Dieckmann Condensation

What are 5 factors of thermodynamic and kinetic products

Kinetic

• Low E_a

• Less Stable

• Low Temperature

• High Energy

• High Product

Thermodynamic

• High E_a

• More Stable

• High Temperature

• Low Energy

• Low Product

no reaction

no reaction

What type of acid or base is benzene?

Lewis Base

How do you calculate formal charge?

Formal Charge = (# valence e-) - (bonds + dots)

Hofmann Rearrangement

Will EDG react faster or slower than a sole benzene ring?

Faster than a benzene ring because it increased electron density

Will EWG react faster or slower than a sole benzene ring?

Slower than a benzene ring because it decreases electron density

What order of substitution does radical bromination prefer?

3* > 2* > 1* > methyl

no reaction

Reduction of an acyl chloride with LTBA results in the formation of:

aldehyde

What is the difference between concentrated H₂SO₄ and dilute?

• concentrated dehydrates and causes a double bond

• dilute adds an -OH group

What is the order of least to most readily oxidized?

methyl < alcohol < aldehyde < CO_z

What is the order of most to least reactive of addition-elimination reactions?

carboxylic acid derivatives:
acid halide > anhydride > ester > amide