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Review for Orgo 2 Exam (that i keep forgetting)

front 1

hydrates

back 1

gem diol

reaction Reversible to an aldehyde/ketone

Relatively stable by the electron-withdrawing groups

front 2

Hemiacetal

back 2

OH and OR

Can occur under acidic, basic, neutral conditions

Reversible like hydrates

front 3

Intramolecular Hemiacetal formation

back 3

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)

front 4

Reaction of Acetal

back 4

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

Undergo one reaction which is hydrolysis (H3O+

front 5

Acetal Protection Group

back 5

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

front 6

Thioacetals

back 6

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

front 7

Degree of Unsaturation

back 7

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

front 8

Hydrocarbon(no rings/double bonds) formula

back 8

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

Pi bond reduce the hydrogen count by 2

front 9

IR spectroscopy

back 9

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

front 10

More important notes of IR

back 10

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

front 11

More info

back 11

Aldehydes(1740-1690)

Ketones (1750-1680)

Esters (1750 -1735)

Carboxylic acids (1780 -1710)

Amide (1690-1630)

Anhydrides (1830-1800) (1775-1740)

front 12

Monoasscharides

back 12

Glucose, Fructose

front 13

Disaccharide

back 13

Sucrose, Maltose, Lactose

front 14

Epimers

back 14

When two diastereomers only different from 1 carbon

front 15

Fisher Projects for Glycosides

back 15

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

front 16

Glycosides formation

back 16

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

Carbon 1: Down = Alpha

front 17

Reducing Sugar for Carbohydrates

back 17

Hemiacetal and Aldehydes/ketones

front 18

p - Toluidine

back 18

front 19

Morpholine

back 19

front 20

Pyrrolidine

back 20

front 21

Diethylamine

back 21

front 22

Acetophenone

back 22

front 23

Lactone

back 23

front 24

Ranking Nucleophiles

back 24

- 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