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Organic Chemistry Exam 2 Cheat Sheet by

CHM 221, this covers units 4-6

Terms to know

Markov­nikov's rule
in addition reactions, the proton is added to the carbon atom with the greatest number of hydrogen atoms attached to it
anti-M­ark­ovn­ikov's rule
in addition reactions, the proton is added to the carbon atom with the lowest number of hydrogen atoms attached to it
zaitsev's rule
in elimin­ation reactions, the major product is the more stable alkene with the highly substi­tuted double bond

M, Anti-M and V

Elimin­ation Reactions

E1
multistep,
E2
single step,

Terms

Protic
Solvents with O-H or N-H bonds and the ability to hydrogen bond
Aprotic
Solvents that dont
Nucleo­phile
A simple metal and salt, nucleus "­lov­ing­", usually anions
Electr­ophile
Must contain a C-LG bond, electron "­lov­ing­", usually cations
Solvolysis Reaction
the nucleo­phile is also the solvent
E/Z System
1. Prioritize the 2 groups attached to each carbon relative to one another. If the higher priority groups are cis, its Z, it their trans, its E
 

Terms

Vicinal
2 atoms or groups bonded to same carbon
Geminal
2 atoms or groups beonged to the same side of the carbon
syn-ad­dition
added to same plane or same side of compound
anti-a­ddition
added to different sides of compounds

Geminal vs Vicinal

Anti vs Syn

Substi­tution Reactions

SN1
2 step, RR possible, tertiary reacts fastest
SN2
1 step, no RR, Primary reacts fastest

Elimin­ation and Substi­tution Flowchart

 

Addition Reactions

Names of Reaction
Kind of Reactant
Whats on Arrow
Product structure
Catalytic Hydrog­enation
Alkene
H2 , Ni, Pt or Pd
alkane, M not applic­able, syn, No RR
Addition of hydrogen halides
Alkene
H-X
M, No syn/anti, RR possible
Acid Catalyzed hydration
Alkene
H2SO4 or H+, H2O
New H and OH added, M, no syn/anti, RR possible
Hydrob­ora­tio­n-O­xid­ation
Alkene
1. B3H6, 2. H20, -OH
New H and OH added, Anti-M, Syn, no RR
Addition of Haloge­ns/­hal­oge­nation
Alkene
X2, CH3Cl
new vicinal halogens, M not applic­able, Anti, No RR
Cohalo­gen­ation
Alkene
Br2, H2O
new halogen and OH, M of OH and Anti-M for halogen, Anti, No RR
Expoxi­dation
Alkene
RCOO-OH (peroxide)
Expodie is formed, M not applic­able, Syn, No RR
Ozonolysis
Alkene
1. O3, 2. H2O
2 carbonyl compounds, nothing else applicable
M=Mark­ovn­ikov's Rule
Anti-M= Anti-M­ark­ovn­ikov's Rule
RR=Rea­rra­ngement
                   
 

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