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Organic Chemistry ACS Study Guide Cheat Sheet by

acs

Combustion

Complete
__ + O2 --> CO2 + H2O
Incomplete
__ + O2 --> CO +H2O
 
__ + O2 --> C +H2O
Alka­ne/­Ether

Balance Carbon> Hydrog­en> Oxygen

Haloge­nation

Alkene
H2C=CH2 + Br2 --> H2C(Br­)CH­2(Br)
Alkyne
same as alkene, but double addition reagent
+Cl2 or Br2

Addition of Simple Acids

Alkene
CH2=CH­2+HCl --> CH3-CH­2(Cl)
Alkyne
Same as Alkene, but twice addition reagent
+HBr or HCl

Marko­vni­kov's Rule: Hydrogen goes to Carbon with more Hydrogen; the rich get richer

Hydration

Alkene
H2C=CH2 + H-OH --> CH3-CH­2(OH)
Alkyne
Same as Alkene, but twice the addition reagent
+H2O & Acid Catalyst (Pt, Pd, Ni)

Marko­vni­kov's Rule: the rich get richer

Hydrog­enation

Alkene
H2C=CH2 + H2 --> CH3-CH3
Alkyne
Same as Alkene, but twice the addition reagent
Alde­hyde
CH2(O) + H2 --> CH3(OH)
Ketone
H3CC(O)CH3 + H2 --> H3C-CH­(OH­)-CH3
Alkene­/Alkyne --> Alkane
Aldehyde --> Primary Alcohol
Ketone --> Secondary Alcohol
 

Polyme­riz­ation

Addition
CH2=CH­+CH­=CH­2--­>CH­2-C­H2-­CH2-CH2
Conden­sation
(OH)C(­O)-­(O)­C(OH) + HO-CH2-OH -->
Polyamides
(Cl)C(­O)-­(O)­C(Cl) + H2N-NH2 -->
Addition Polyme­riz­ati­on: linking together many Alkene molecules through addition reactions

Carb­oxylic Acid: Conden­sation

Amide: Polyamide

Substi­tution

Arom­atic
Switch 1 Hydrogen with one of the addition reagents
Aromatics= stable­/ch­emi­cally inert

Dehydr­ation

180*C
H3C-CH­2(OH) --> H2C=CH2 + H2O
140*C
H3C-OH + H3C-OH --> H3C-O-CH3 + H2O
@180*C Alcohol --> Alkene
@140*C Alcohol + Alcohol --> Ether

Requires Acid Catalyst (H2SO4)

Oxidation

 
Primary Alcohol --> Aldehyde
Secondary Alcohol --> Ketone
Tertiary Alcohol -- NR
Aldehyde --> Carboxylic Acid
Ketone --> NR
Thiols --> Disulfide

Oxid­izing Agents: K2Cr2O7; KMnO4

Tollens Reagent: 2Ag(NH­3)2+ --> 2 Ag

Bene­dicts Reagent: 2Cu2+ --> Cu2O
(blue) --> (red precip­itate)
 

Dissoc­iation

 
Acid: Carboxylic Acid, Phenol
Donate H from -OH to H2O --> O- +H3O+

Base: Amine
Steal H from H2O --> NH_+ + OH-

Acid + H2O -->

Base + H2O -->

Neutra­liz­ation

 
Acid + Base --> Salt + H2O

Salt Ex) O-K+

Base: KOH, NaOH
Acid: Phenol, Carboxylic Acid

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