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Organic Chemistry I Reactions Cheat Sheet, Cheat Sheet of Organic Chemistry

Laney CollegeOrganic Chemistry

Organic reactions organized by compound files and reaction types

Typology: Cheat Sheet

2020/2021

Uploaded on 04/26/2021

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ekayavan 🇺🇸

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!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!H.!Kim!for!Chem!30B!
1!
Handout:)Organic)Chemistry)Reactions)
)
)
Reactions)Organized)by)Compound)Families)
!
Alkanes!
1.!Combustion!
2.!Halogenation!
!
Alkenes!and!Alkynes!
1.!Additions:!hydrogenation,!halogenation,!!
!!!!!!!!!!hydrohalogenation,!hydration!
2.!Polymerization!
!
Aromatic!Compounds!
Substitutions:!nitration,!halogenation,!sulfonation!
!
Alcohols!
1.!Elimination:!dehydration!
2.!Oxidations!
!
Thiols!
Oxidation!
!
Amines!
Acid-Base!reactions!
!
Aldehydes!and!Ketones!
1.!Addition:!Acetal/hemiacetal!formation!by!alcohol!!
!!!!!addition!
!!!!!(Reverse!rxn:!Acetal!hydrolysis!with!acid)!
2.!Oxidation!and!Reduction!for!aldehydes!
!!!!(*Ketones!go!through!reduction!only)!
!
Carboxylic!Acids!!
1.!Substitutions:!esterification,!amidation!!
!!!!(Reverse!rxns:!ester!hydrolysis!with!acid!or!base,!amide!hydrolysis!with!acid!or!base)!
2.!Acid-base!reactions!
!
Phosphoric!acid!and!Phosphates!
Phosphoric!acid:!Esterification!with!alcohol!
Phosphates:!Phosphorylation!
! !
pf3
pf4

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Download Organic Chemistry I Reactions Cheat Sheet and more Cheat Sheet Organic Chemistry in PDF only on Docsity!

Handout: Organic Chemistry Reactions

Reactions Organized by Compound Families

Alkanes

1. Combustion

2. Halogenation

Alkenes and Alkynes

1. Additions: hydrogenation, halogenation,

hydrohalogenation, hydration

2. Polymerization

Aromatic Compounds

Substitutions: nitration, halogenation, sulfonation

Alcohols

1. Elimination: dehydration

2. Oxidations

Thiols

Oxidation

Amines

Acid-Base reactions

Aldehydes and Ketones

1. Addition: Acetal/hemiacetal formation by alcohol

addition

(Reverse rxn: Acetal hydrolysis with acid)

2. Oxidation and Reduction for aldehydes

(*Ketones go through reduction only)

Carboxylic Acids

1. Substitutions: esterification, amidation

(Reverse rxns: ester hydrolysis with acid or base, amide hydrolysis with acid or base)

2. Acid-base reactions

Phosphoric acid and Phosphates

Phosphoric acid: Esterification with alcohol

Phosphates: Phosphorylation

Reactions Organized by Reaction Type

Family Reaction Example

1. ADDITION

Alkenes and

alkynes

Hydrogenation

Halogenation

Hydro-

halogenation

Markonikov’s Rule

applies: H adds to C

with more Hs already.

Hydration

Markonikov’s Rule

applies.

Aldehydes

and ketones

Addition of

alcohol to get

hemiacetals or

acetals

2. SUBSTITUTION

Aromatic

compounds

Nitration

Halogenation

Sulfonation

Carboxylic

acids

Esterification

with alcohol

Amidation with

amine

Phosphoric

acid and

Phosphates

Phosphoric acid:

Esterification

with alcohol

Phosphates:

Phosphorylation

C C
H
H
H
H
+ H 2

Pd catalyst C C H H

H
H
H H

H C C H C C H H H H H H

  • 2 H 2 Pd^ catalyst C C
H
H
H
H
  • Cl 2 (or Br 2 ) (^) C C H H
H
H

Cl Cl H 3 C C O H(R) + CH 3 CH 2 OH H^3 C^ C OH H(R) O CH 2 CH 3 hemiacetal H 3 C C O H(R) O CH 2 CH 3 CH 2 CH 3 acetal H+^ catalyst (^) + CH 3 CH 2 OH H+^ catalyst

  • H 2 O

+ HNO 3

H 2 SO 4 catalyst NO^2

  • Cl 2 (or Br 2 )

FeCl3 (or FeBr3) catalyst^ Cl

+ SO 3

H 2 SO 4 catalyst SO^3 H

H 3 C C
O
OH +^ CH 3 CH 2 OH

H+^ catalyst H 3 C C

O
OCH 2 CH 3 + H 2 O
H 3 C C
O
OH +^ CH 3 NH 2

heat H 3 C C

O
NHCH 3 + H 2 O
HO P
O
OH +^ CH 3 OH
OH
HO P
O
OCH 3
OH
+ H 2 O

O P O O (^) + ROH O- RO P O O- O- Adenosine P O P O- + Energy O O O-^ O- O P O O O- Adenosine P O- O O-

C C
H
CH 3
H
H
  • HCl (or HBr) (^) C C H CH 3
H
H

H Cl C C

H
CH 3
H
H

+ H 2 O C C H

CH 3
H
H

H+ catalyst^ H^ OH

Other Reaction Types

*Note that organic chemistry reactions can be classified in several different ways.

Family Reaction Example

RADICAL REACTIONS

Alkanes Combustion

(Also

oxidation/reduction

reaction)

Halogenation

Mixed products

Alkenes Polymerization

HYDROLYSIS

Esters

(Reverse rxns of

carboxylic acid

esterification)

Acid hydrolysis to get

carboxylic acid and

alcohol

Saponification: Base

hydrolysis to get

carboxylic acid salt and

alcohol

Amides

(Reverse rxns of

carboxylic acid

amidation)

Acid hydrolysis to get

amine

Base hydrolysis to get

amine

Acetals

(Reverse reaction

of acetal formation

from

aldehydes/ketones)

Acid hydrolysis to get

aldehydes of ketones

(reverse of acetal

formation)

CH 4 (g) + 2O 2 (g)

heat

CO 2 + 2H 2 O + Heat

CH 3 CH 2 CH 3 + Cl 2

light or heat

HCl + CH 3 CH 2 CH 2 Cl + CH 3 CHCH 3 Cl CH 2 CH 2 CH 2 Cl Cl CH 2 CHCH 3 Cl CH 3 CCH 3 CHCH 2 CH 3 Cl Cl Cl Cl Cl

+ +^ +^ +
CH 3 CH CH 2 C
H
H 2
C C
H
H 2
C
CH 3 CH 3

( )

initiator

R C
O
O

H+^ catalyst

R C
O
CH 3 + H 2 O OH +^ CH 3 OH
R C
O
O R C
O

CH (^3) O– (^) Na++ CH 3 OH

H 2 O

  • NaOH (aq) H+^ catalyst H 3 C C
O
H 3 C C +^ H 2 O^ OH + CH 3 NH 2
O
H
N CH 3
H 3 C C
O
H 3 C C
O
OH
H

N CH 3 +^ NaOH^ (aq)^ + CH 3 NH 2

H 2 O

H
H 3 C C O H
  • (^) catalyst H 3 C C
O
CH 2 CH 3 + H 2 O OH+ 2 CH 3 CH 2 OH
O CH 2 CH 3