hydrates

gem diol

reaction Reversible to an aldehyde/ketone

Relatively stable by the electron-withdrawing groups

Hemiacetal

OH and OR

Can occur under acidic, basic, neutral conditions

Reversible like hydrates

Intramolecular Hemiacetal formation

Alcohol + Aldehyde will most likely form a cyclic hemiacetal

Cyclic hemiacetal can revert to acyclic alcohol by NaBH4

PADE P(protonation) A(addition) D(deprotonation) E(elimination)

Reaction of Acetal

Are locked and not reversible so no reaction can take place after an acetal formation

Undergo one reaction which is hydrolysis (H3O+

Acetal Protection Group

A Grignard reagent cannot be used with aldehydes or ketones, as it will react with them immediately.

We can use ethylene glycol or Ch3OH H+ to protect

Thioacetals

Raney Ni (reduces to alkanes) as well as the wolff-kisher and clemmensen

Degree of Unsaturation

Formula: 2C+2+N-H-X/2

Hydrocarbon(no rings/double bonds) formula

Key Pattern formula: # Hydrogens = 2 x (# of Carbons) + 2

Pi bond reduce the hydrogen count by 2

IR spectroscopy

3600 – 2700 cm^-1X-H (single bonds to hydrogen)

2700 – 1900 cm^-1 X≡X (triple bonds)

1900 – 1500 cm^-1 X=X (double bonds)

1500 – 500 cm ^-1X–X (single bonds)

3000 border between alkene(above) and alkane(below)

dont look for degrees of unsat if there isnt any

More important notes of IR

3400-3200 (OH appear)

1850 -1630 (C=O) [like swords]

3200 Amines and Amides Appear

- Primary Amine: 2 stretched-out small peaks (like balls)

- Secondary Amine: 1 long stretch peak

- Primary Amide: 2 peaks a little more spaced out (like boobs

- Secondary Amide: 1 long a little open peak further down

(rare) Triple bond region around 2050-2250 cm^-1

More info

Aldehydes(1740-1690)

Ketones (1750-1680)

Esters (1750 -1735)

Carboxylic acids (1780 -1710)

Amide (1690-1630)

Anhydrides (1830-1800) (1775-1740)

Monoasscharides

Glucose, Fructose

Disaccharide

Sucrose, Maltose, Lactose

Epimers

When two diastereomers only different from 1 carbon

Fisher Projects for Glycosides

OH on the right (goes down)

OH on the left (goes up)

5 carbon OH on the right is (D)

5 carbon OH on the left is (L)

5 and 6 carbon bonds rotates during glycoside formation and if OH is down, it does not become up. If up down

Glycosides formation

Carbon 1: Up = Beta (more predominant) (more likely seen)

Carbon 1: Down = Alpha

Reducing Sugar for Carbohydrates

Hemiacetal and Aldehydes/ketones

p - Toluidine

Morpholine

Pyrrolidine

Diethylamine

Acetophenone

Lactone

Ranking Nucleophiles

- Steric hinderance lowers reactivity 1 > 3

- The bigger the group the more polarizable the more reactive

- Needs a negatively charge atom to be more reactive

- Oxygen is more electrophilic so is less nucleophilic than nitrogen becomes less reactive when comparing the two; Nitrogen becomes unstable more reactive