Orgo 2 Exam 3 Mech

Front 1

a

Back 1

a

Front 2

b

Back 2

b

Front 3

c

Back 3

c

Front 4

cyclic product look to pos

Back 4

intramolecular rxn

Front 5

form an ester

reverse

Back 5

snks

Front 6

ketone to alkane

additional carbons

Back 6

wittig rxn

djdkdkkr

Front 7

carboxylic deriv to ketone

Back 7

nrjej

Front 8

ketone to ester

Back 8

bayer villiger

peroxi acid

RCOOOH

Front 9

reduce ketone to alkane

basic

Back 9

wolff kishner reduction

NH2NH2, NaOH, DMSO

Front 10

reduce ketone to alkane

acidic

Back 10

clemson reduction

Zn(Hg), HCl

Front 11

base halogenation of ketone

Br replaces alpha hydrogen

Back 11

Br2 OH-

Front 12

aldol condensation rxn

(intramolecular)

Back 12

will favor a 5 or six membered ring

Front 13

crossed aldol

Back 13

2 different different carbonyl compounds

the alpha H will attach the carbonyl carbon

Front 14

aldol initial product

Back 14

Beta hydroxy carbonyl

Front 15

aldol condensation reaction

final product

Back 15

Alpha Beta unsaturated carbonyl

Front 16

iodoform test

Back 16

presence of methyl ketone

Front 17

phenylhydrazine

Back 17

pg6

fnfkfk

Front 18

why anhydride is more reactive than an ester

Back 18

better leaving group (acetate better than ethoxide)

Front 19

acetic anhydride

Back 19

H3CC=O-O-C=OXH3

(CH3CO)2O

O O

|| ||

CH3-C-O-C-CH3

Front 20

Ph-CH2Cl

+ NaCN

Back 20

forms cyano hydrin

sn2

Ph-CH2CN

Front 21

Ph-CH2CN

H2SO4

reflux

Back 21

Ph-CH2COOH

11.

Front 22

what will not undergo hydrolysis

(in w/ acid or base present)

Back 22

ketone

12.

Front 23

13

Back 23

nmr review

Front 24

acetoacetic ester

Ch3C=OCH2C=O-O-CH2CH3

add r to alpha hydrogen

Back 24

1) NaOC2CH3 (same group limit competition)

2) RBr

Front 25

dicaebonyl ester to CA

Back 25

1) NaOH

2) H3O+ (CA)

3) Heat (split at alpha carbon)

Front 26

ester enolate

Back 26

deprotonated alpa carbon

2 resonense

15.

Front 27

strength of acid

Back 27

melonic acid> di CA w/o the same resonance

Front 28

nomenclature ester

ketone

aldehyde

Back 28

17

Front 29

tollens test 2,4-DNP

distinguishes

Back 29

ketones and aldehydes

18.

Front 30

C=N is called

Back 30

imine

18b.

Front 31

initial product of aldol reaction

Back 31

Beta hydroxy carbonyl

Front 32

only Carboxilic Acid derivitive with 2 carbonyl groups is

Back 32

anhydride

RC=OOC=OR'

Front 33

base promoted hydrolysis of ester called

Back 33

soponification

Front 34

malonic ester synthesis is the synthetic equivolent used to make substituded

Back 34

Acetic acids

Front 35

1° amine to Nitrile

R-NH2 to R(trip)N

Back 35

P4O10

Front 36

propanamide

Back 36

CH3CH2C=O

\

NH2

Front 37

5-oxo-4-propylhexanoic acid

Back 37

Carboxylic acid

Carbonyl Carbon is 1

carbon 4 has prop group

carbon 5 has carbonyl

Front 38

enolate from

acetalacetone pentane 2,4 dione

Back 38

deprotonat the alpha H

first is the charged carbon

3 other resonance

Front 39

hemi acetal mech

Back 39

protonate carbonyl

nucleophile addition

resonense

addition

regen

21.

Front 40

long molecule with

OH and CA group

H2SO4

H2O

Back 40

intramolecular esterification

(lactone)

protonate carbonyl

resonance

deprotonate

protonat leaving group (H2O)

reform carbonyl

deprotonate

Front 41

intramolecular esterificarion

mech

Back 41

·addition

·proton transfer

·reform/elimination

·deprotonate reform cat.

Front 42

aldol exn

alpha beta unsaturated carbonyl

Back 42

OH-

Heat

Front 43

alkyne to ketone

hydration of alkyne

Back 43

HgSO4

H2SO4

H2O heat

Front 44

acid halide

to

ester

Back 44

R-OH pyridine

Front 45

acid halide and amide group on one molecule

heat

Back 45

intramolecular reaction

cyclic NH join at carbonyl carbon

wittig reaction

Front 46

acid halide to add R group to carbonyl carbon

Back 46

(R)2CuLi

cuprate

Front 47

1 methylcyclohexane

to 1methy1bromohexane

Back 47

Br2 hv (or heat)

Front 48

1methy1bromocyclohexane

to 1methy1cyclohexene

Back 48

NaOH/heat

Front 49

1methy1cyclohexene

to

2methy 1cyclohexanol

Back 49

1)BH3, THF

2)H2O2, NaOH

hydroboration

Front 50

oxidate 2° alcohol to ketone

Back 50

oxidizer

e.g.

H2CrO4

Front 51

ketone to imine (C=N-R)

Back 51

(R)NH2

addition dehydration

Front 52

CA to acid chloride

Back 52

PCl3

or SOCl2

Front 53

acid halid to amide at alpha carbon

Back 53

NH3 excess

Front 54

amide to nitrile

Back 54

P4O10 heat

Front 55

acid chloride

add R group

Back 55

(R)2CuLi

ether -78°C

Front 56

ethyl actoacetate

CH3COCH2COOC2H5

add R group to alpha carbon

then form CA (split at alpha carbon)

Back 56

1)NaOCH2CH3

2) R-Br

3) NaOH

4) H3O+

5) heat

Front 57

Ketone to ester

Back 57

RCO3H

Front 58

CA to 1° alcohol

Back 58

strong reduction

1)LiAlH4

2)H2O

Front 59

primary alcohol to primary bromide

Back 59

PBr3

Front 60

ketone

Ph-COCH3

with

HONH2

H+

Back 60

Ph-C=N-O

\

CH3

Front 61

ketone

replace all alpha hydrogens with

Deuterium

Back 61

1)NaOD excess

2)D2O

Front 62

primary alcohol to aldehyde

Back 62

PCC

Front 63

diethyl melonate

to 3 methylpentanoic acid

Back 63

1)NaOCH2CH3 (base same group)

2) CH3CHBrCH2CH3

3)NaOH (Soponification)

4)HCl (Acididication ,CA formes)

5) heat (decarboxylates)

Front 64

compound with ketone and ester

reduce ester

keep ketone

Back 64

1)HOCH2CH2OH/H+

2) LiAlH4

remove protecting group with acid at the end H+