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OChem Review

front 1

MeOH -----> H+

back 1

Glycoside formation. Turns all substituents into OMe but the CH2OH

front 2

CH3-I ------> Ag2O

back 2

Methylation. Turn all substituents into OMe including the CH2OH.

front 3

H2O-----> H+

back 3

Hydrolysis. Turns the anomeric substituent into an OH and leaves a floating H+ in solution.

front 4

HNO3

back 4

Reduces/Oxidizes. Turns the top and bottommost carbons into CO2H

front 5

An optically inactive molecule is ________

back 5

Symmetrical or has a plane of symmetry

front 6

An optically active molecule is ________

back 6

Not symmetrical. Does not have a line of symmetry.

front 7

NaBH4

back 7

Turns the top and bottom ends of the structure into OH

front 8

(1) HCN (2)Pd/H2 (3) H3O+

back 8

Adds an OH in both the D and L configuration. Results in 2 epimers. Kiliani Fischer Reaction

front 9

(1) H2NOH

(2) Ar2O

ArONa

(3) NaOMe

MeOH

back 9

Wohl's Degradation. An OH is removed from the structure.

front 10

LiAlH4

back 10

Gets rid of the C=O group in the structure, but leaves everything else the same

front 11

(1) NaBH4 or NaBH3CN or H2/Ni

back 11

Combines 2 structures at a Nitrogen and gets rid of an H2O (A =O and 2Hs)

front 12

NH3 and then NaBH4

back 12

Adds the NH3 to the alpha carbon to become NH4 and then H2O leaves.

front 13

Anytime you see a Br2 on top with another reagent at the bottom

back 13

Replace that alpha hydrogen with the Br. Do not have the Br be a leaving group.

front 14

Anytime you see an LDA with N(---)

back 14

It deprotonates the alpha hydrogen somewhere and makes an anion. Use when there is only 1 C=O because it is bulky

front 15

H3O+

back 15

Turns the important thing something into OH

front 16

When exposed to heat

back 16

A CO2 is lost, C=O with another OH. Crazy, I would have done so well on exams if I knew

front 17

A Br with NaOMe and OMeH

back 17

Replace the CH3s with Br and have is act as a LG

front 18

Claisen Condensation

back 18

Needs 2 alpha hydrogens to work. Then add that same molecule to itself at the alpha hydrogen position

front 19

NaOEt/EtOH

back 19

Use when there are 2 C=O present because its small

front 20

When it backside attacks, just combine the OH together

back 20

no data