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Organic Chemistry Reactions: A Comprehensive Guide for Students, Study notes of Organic Chemistry

A comprehensive overview of organic chemistry reactions, covering key concepts, mechanisms, and examples. It delves into various reaction types, including alkene, alkyne, and ketone/aldehyde reactions, with detailed explanations of each step. Particularly useful for students studying organic chemistry, offering a structured and organized approach to understanding these fundamental reactions.

Typology: Study notes

2023/2024

Uploaded on 03/13/2025

benjamin-jamal
benjamin-jamal 🇺🇸

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All Organic Chemistry Reactions
Everything to know for each reaction —>
I. Alkenes
A. Carbocation Pathway
1.Addition of Halides (H-X)
i. Addition of HBr
ii. Addition of HCl
iii. Addition of HI
2.Acid Catalyzed Electrophilic Addition
i. Acid Catalyzed Addition of Water
ii. Acid Catalyzed Addition of Alcohol
iii. Acid Catalyzed Addition of Carboxylic Acid
3.Rearrangements
B. 3 Membered Ring Pathway
1.Halogen Addition
i. Bromination
a. In Presence of Water
b. In Presence of Alcohol
2.Oxymercuration-Reduction
i. With Alcohol As Solvent
C. Concerted Pathway
1.Hydroboration-Oxidation
2.1,2-Dihydroxylation
3.Catalytic Hydrogenation
D. Ozonolysis
II. Alkynes
A. Catalytic Hydrogenation
1.To Alkane
2.Lindlar
3.To (E) Alkene
B. C(sp)-C(sp3) bond formation
1.Alkynyl Anion Formation
2.SN2 with Alkyl Halide
C. Addition
1.Hydrohalogenation
2.Halogen Addition
3.Hydration
i. Acid Catalyzed
ii. Hydroboration-Oxidation
III. Ketones and Aldehydes
A. Enol-Keto Tautomerism
~
X
~
~
~
~
~
w
~
~
~
X
~
X
-
Nucleophile
:
Provides
er
pair
to
form
new
siralent
bond
,
Levis
Ben
-
Electrophile
:
Accepts
e
pair
to
form
new
covalent
bond
,
Lewis
Acid
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff
pf12
pf13
pf14
pf15
pf16
pf17
pf18

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All Organic Chemistry Reactions

Everything to know for each reaction —>

I. Alkenes

A. Carbocation Pathway

1.Addition of Halides (H-X)

i. Addition of HBr

ii. Addition of HCl

iii. Addition of HI

2.Acid Catalyzed Electrophilic Addition

i. Acid Catalyzed Addition of Water

ii. Acid Catalyzed Addition of Alcohol

iii. Acid Catalyzed Addition of Carboxylic Acid

3.Rearrangements

B. 3 Membered Ring Pathway

1.Halogen Addition

i. Bromination

a. In Presence of Water

b. In Presence of Alcohol

2.Oxymercuration-Reduction

i. With Alcohol As Solvent

C. Concerted Pathway

1.Hydroboration-Oxidation

2.1,2-Dihydroxylation

3.Catalytic Hydrogenation

D. Ozonolysis

II. Alkynes

A. Catalytic Hydrogenation

1.To Alkane

2.Lindlar

3.To (E) Alkene

B. C(sp)-C(sp3) bond formation

1.Alkynyl Anion Formation

2.SN2 with Alkyl Halide

C. Addition

1.Hydrohalogenation

2.Halogen Addition

3.Hydration

i. Acid Catalyzed

ii. Hydroboration-Oxidation

III. Ketones and Aldehydes

A. Enol-Keto Tautomerism

~

X

↑ ↑ (^) ~

~ ~ ~ ~ w ~ ~ ~ X ~ X

  • (^) Nucleophile

: Provides er (^) pair to^

form (^) new siralent (^) bond ,

Levis

Ben

  • Electrophile

: Accepts e pair to^ form new covalent^

bond ,

Lewis Acid

Addition of HBr

Hydrohalogenation

Hey

Bonds

Formed

Bonds

Broke

· C- Br

Summary

· C

  • H

· H-Br

3r

R

H

  • 1

uBr

&egiozhem

Markornikov

Stereochem

  • Random

Y

Che

Cl- A^

M

Alkene Alky1 Bromide

Mechanism

S Sa

Br

H-Br

&

3r e

I

  • ^

V

H -^

X

electrophilic attack^

nucleophilic trepping

Examples Limitations

Addition

of (^) HL)" HE follow same^

process

Reactivity

decreases as atom size^ increases

MB r

HCl

HE

Acid Catalyzed Addition of Alcohol

Akrhol Addition^

↓ y

Bonds foreed Bonds (^) Broke

  • other formation · -^

0 · C

  • C(n)

masO

in

a

no

· C

  • H. O - H

Ij

... (^) S R

Regrochem

: (^) Markovnikov Stereochen^

: Random

Altere

Ether

has CHOH CHOHr^

+ Hs0 + H- -Iz

  • O CH - ⑪

H

--

or

W

i

H

jo

R

-z

ja

  • 1 -^

x (^) -

1

R

I I

Exeples

limitations

·

Alcohol

must be (^) MePH

or a^10 alcohol

Acid Catalyzed Addition of

Carboxylic Acid

key

Bonds formed

Key

Bonds Broken^6

·^ ((n) (-

Summary

t

· C

  • H
· 0 -H

& 17

N (^) I'M

Reochem

: (^) Markownikov Stereochem^

: Random O

Alken z

↑ of Ester

ha CLOON

Cl00e

  • Hs0 +

i ...

o

H &^ or

H- - - r

& (^) - O -

O H II &

  • O

I 1 H

H

  • (^) 0-

jo

n

ja

I H H^ -

1 -z -

xp

R

I I

Examples (^) Limitations

Bromination in the Presence of Water

key

Bonds formed Key Bonds^

Broken BC

~ Halohydrin

formation

· C- OH^

  • C

     C(π) 

Summary

H · C-Br

· Br-Br

R &

H

,

1

-H + HBr

n

L

on

  • J R

R

R

Regiochem

:

Markovik

a Stereochen

: Anti

enant. -

Alter

Alcohol

Mechanism

B -Br

R

↑↓-

Bro an ↑ I^ -

H

=

  • I S - H Br

-1) , L I^ H

↑= wi

, (^1519) H &^

I J^ It (^) R

I I > - O

/

(^7) -

I

H

I

R R & ↑^

enantiomer

j

-0H .

Br

H (^) I H Br or

can (^) attack

fr a H Br

&

Exeples

Imitations

The more substituted bridged carbon holds more

partial positive^ change

Bromination in the Presence of Alcohol

key

Bonds formed Key Bonds^

Broken BC

~ Halohydrin

formation

· C- OH^

  • C

     C(π) 

Summary

H · C-Br

· Br-Br

R &

Brz

R (^) O

,

1

-H + HBr

n

  • J

L

R ROH

Ver R

R Regiochem

:

Markovik

a Stereochen

: Anti

enant. -

Allane

Ether

Mechanism

B -Br

R

↑↓

Bro an

↑ I^

H

=

  • I
  • S^ -^ H^ Br -1) , L I^ H -- R

↑= wi

I

n

d

J (^) It

  • , 1519

/ 7

I (^) H

R R & ↑^

enantiomer

  • 2 I

j

-0H .

Br

H (^) I H

  • or O Br

Br &

can (^) attack

fr a #1 (^) ↓

Exeples

Imitations

  • The (^) more substituted

bridged carbon^ holds^ more

partial positive^ change

Oxymercuration-Demercuration in

Presence of Acid

H

Bonds formed

My

Bonds Broke^ d

Alcohol Addition

S

Summary 2 ↑

-Me

Et

  • Hg(NA) (^) -M

I NS

    • um (^) OR

D + -

/ (^) ROt

I

Regrochem

: (^) Markovnikov Stereochem : Random

Altern Ether

Mechanism

Same as^ last one

Exples

Imitati eul carboxylic

acid

  • can be (^) 2/ ,

,

or 3" alcohol

Hydroboration- Oxidation

Hydratin

H

Bonds formed

My

Bonds Broke^ d

S

Summary

  • 2

Do

o

H

XXOH

Regrochem

: (^) Anti-Markovnikov Stereochem : Syn (^) (M , OH)

Alkne Alcohol

Mechanism ro a

on

I-

R

For

&

i B

·

H

R

  • o M O

on

a

o

H

& (^) -

  • (^) -
     - : D 
-L

↑ (^) -

41

I'

N

-- - (^) D

  • H (^) + 1 /H
  • i

·

"A D

j

o

Hod H

M of

oh

&

C

  • 41

I ,,,,

  • : D 10-

O I^

=

%

L. H on

H

tenut ↑

BR=OH

-/ D

....

Exeples

tenant

.

. Imitation

e on ester^ or^

an ether Can't

· Sturrs bulk^

: - Bu >^

C >

isopropyl

vcyclohexylsEt? Meph

· when staggered

: ·

poak

I substituents^ that were (^) APP on (^) the allee

· rotate

conforme so

thy

App

· Added (^) RzB" I groups

should be^ gauche

Catalytic Hydrogenation

of Alkene

↓ y

Bonds foreed Bonds^ Broke

S

Summary

2 ↑

T

FY

  • PEO = (^) /metal catalyst

Regrochen

:

N/A

Stereochen : ~or solvent - Syn

Alkem Alkane

Mechanism

D Hz

:

: &

  • T En &

1 -

Y

Pd

m+al

Surface

Exeples

Limitations

functional

group compatibility

  • can be (^) in volecule w) akem

:

phenyl ,

ester ,

alcohol , anime ,

2-

· cannot be in

molecule :^

Ketore

, aldehyde ,

GBr ,

2-

· 2 metal

catalysts

: PtL Pd/(

·

solent

usually

Not

Ozonolysis

↓ y

Bonds foreed Bonds^ Broke

h

S

2

E

-min

  • 78 °^ C Regrochen

: Stereochen :

Alkana 2

ketores/aldehydes

Mechanism -^ - [ o ·...]

  • (^) S a - O i

O O &^

o ⑦

=^0 v L ⑧ -Mu

=!^ / kyrl

G (^) 0-

I S

Mr

  • T

  • · Me

p

L -o^ ozonice

~

T

=

  • t
  • 5017

It

-See

Exeples Limitations

Catalytic Hydrogenation of Alkyne (Lindar’s Catalyst) H Bonds formed yBonds Brok a

S C

H mary · C-H

H - H (z)

Regrochen :

N/A

Stereochen :

  • Syn

Alkyne

Alkma

Mechanism

No

need to know

Exeples Limitations ·

functional

group compatibility

can be (^) in molecula · phenyl ,^ allow , ester ,

alcohol

, amive^ , latir , aldehych, (not altered) C-Cl , C-Br ·

Internal

alkyne

E alko · terminal

alkyne ->

terminal

allee

·

Lindlar's

Catalyst :

Ma/caci

,

Pb

,

quialime

([ITE)

Catalytic Hydrogenation of

Internal Alkyne to (E) Alkene

H

Bonds formed

May BondsBrother

partial

reduction

· C-H

Summary

· C-H

2

A

lig

. Nita Regiochem

: Not Stereochen :

Syn

Alkyne

All

(t)

Mechanism

&

Na atros in^ liquid (^) ammora Eject 12-^ that floats around^

in solution^

(very righ^

NRO i solvated (^) ef

largeRr

a trans is

eisolvated)

"

  • Er (^) + e

sand

~

M

S " . Ye N- M "I

<^2 NaTOENty

H (^) Every strong base)

Exeples

Limitations

· (^) functional

grown

compatibility

:

can be^ in molecule (maltired)^

: allow

,

ethr

,

anive

can't be in mobenze(changed)

:

phenyl (^) ,

katire

, aldehych ,^ ester,

24

c -Br , C-E ,

allcohol

,

Thiol

(MSM)

, ferminal carbox

alkyne

SN2 with Alkyl Halides

  • ((sp)-((sp3) bred formation^

H

Bonds formed

Bonds

Broke

l

o

· (^) L-C

Summary

2 ↑

Na

OE-R

(

-X (^) - R

  • E - (^) ) + NaX

Alky/Halide

Alkynyl

Alkyne

Regrochen

: Stereochen :

Anion

Mechanism

  • HH H
↑ :^

↑ A

d

  • C

--

Nach C^

  • Br => -

+ + Brt^ Nat

S

-- L

Nu backside approach

Exeples

limitations

Requirements

:

  1. (^) Me or 102(sp3)- Br (^) or

<(sp2)

  • F
I-CH

In

Br- (^) CHz

Br3i

Bru

Br - E

C(sp)

No H-

,

H-s ,

H-

, c group

in electrophile

(pka224)

  • exothermic (^) acd base rxn happens - 10

fold faster the^ L--bond

formation

Electrophilic Addition to Alkynes

H

Bonds formed

My

Bonds Broke d

S

Summary

= zegHr^

  • But

2

M

T

A , Ch

Alkene

unreacted

Rochen

: Markovikov

Stereochem : Random

Alkym Alkase^ alkym

M

He

dibromo

Bur

geminal

Alkane

Mechanism

20 alkeny/

carbocation

Y

Some allowe also reacts into

M

= - alkane

y

H

a some in^ this case

Brd

can meact trop or bottom

Exeples

limitations

·

fleat needed

·

No

rearragements

of

alkeny'

carbocations

· Alkeny)

halide

computes

v/

alkyne for AX

present

in solution