Question

In: Chemistry

Create a study sheet for organic functional groups. Would be so grateful if someone could check what I have and add anything else that comes to mind:

1. Alcohols: R-OH

Polar, hydrogen bond so are very soluble in water.

Protonate with acid. -OH becomes good leaving group by conjugate base

Deprotonate with Strong Base

2. Ether: R-O-R

Slightly polar, low reactivity

Acts as Lewis Base in Strong Acid

3. Amine: R-N-H2 (primary, secondary, tertiary)

Base.

Polar, hydrogen bond so are very soluble in water.

If 4th bond becomes a positively charged intermediate

4. Ester: RCOOR

CH4 is weakly acidic, deprotonate with Strong Base.

Weakly electrophilic Carbonyl Carbon, requires Strong Nucleophile to attack

5. Amide RCONH2

Can Hydrogen Bond, but are only water-soluble if small amides

6. Hemiacetal/hemiketal:

Polar, soluble in water. Not electrophilic.

7. Mesyl/Tosyl Groups:

Nonpolar

Basic

Good Nucleophiles

8. Hydrazine/hydrozone: N-N or R-N-N

Basic

Solvent ?

Good Nucleophiles.

Good Lewis Bases

9. Nitrile: CN-

Slightly polar

Strong Nucleophile

10. Epoxide:

Slightly polar

Basic

11. enamine/imine:

Slightly Polar

Basic

Good Nucleophile

12. Nitro: RNO2

Polar

Good Electrophile and Nucleophile

13. Nitroso: N-O

Polar

Strong Nucleophile and base

14. Oxime:

Very Polar, Hydrogen bonding, very soluble in water

Solutions

Expert Solution

All of your assumptions are correct and enough for given functional groups.

1. Alcohols: R-OH

Polar, hydrogen bond so are very soluble in water.

Protonate with acid. -OH becomes good leaving group by conjugate base

Deprotonate with Strong Base

2. Ether: R-O-R

Slightly polar, low reactivity

Acts as Lewis Base in Strong Acid

3. Amine: R-N-H2 (primary, secondary, tertiary)

Base.

Polar, hydrogen bond so are very soluble in water.

If 4th bond becomes a positively charged intermediate

4. Ester: RCOOR

CH4 is weakly acidic, deprotonate with Strong Base.

Weakly electrophilic Carbonyl Carbon, requires Strong Nucleophile to attack

5. Amide RCONH2

Can Hydrogen Bond, but are only water-soluble if small amides

6. Hemiacetal/hemiketal:

Polar, soluble in water. Not electrophilic.

7. Mesyl/Tosyl Groups:

Nonpolar

Basic

Good Nucleophiles

8. Hydrazine/hydrozone: N-N or R-N-N

Basic

Solvent ?

Good Nucleophiles.

Good Lewis Bases

9. Nitrile: CN-

Slightly polar

Strong Nucleophile

10. Epoxide:

Slightly polar

Basic

11. enamine/imine:

Slightly Polar

Basic

Good Nucleophile

12. Nitro: RNO2

Polar

Good Electrophile and Nucleophile

13. Nitroso: N-O

Polar

Strong Nucleophile and base

14. Oxime:

Very Polar, Hydrogen bonding, very soluble in water

queen_honey_blossom answered 1 year ago

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