-these two reagents can form ions by pulling terminal Hydrogens off. 

-Forms the acetylide Ion, or any O^-

• A strong acid can porotonate a alkene or an alkyne, which can futher more create a carbocation. 
• the first Hydrogen on a multiply bond will be on the least substituted Carbon, which forms the most stable carbocation.
• Usually used as an acid catalyst. 

• Same as H₂SO₄ in the way it attacks. 
• the Cl^-  will attack the carbocation of the  alkyne. 
• there can also be carbocation rearrangement during this step. 
• this can form Geminal dihalides

• this will put the X atom on both ends of the triple bond. 
• If Cl₂ is in excess there will be four Cl's bonded to the original triple bond. 
• The Cl will form an "epoxide" like bond. This will make the other Cl come in from the backside fo backsided attack. 

• these two reagents will react with an aklyne to form an enol, and then to go on to form a Keto molecule. 
• The H will first protonate the the least substituted to the Carbon.

H₂, Pd/C + alkyne

or 

H₂, Pt/C + alkyne

• both of these reactions will send alkynes to alkanes. 
• they do not stop at the formation of the alkene. 

• this will form the aklene with cis addtion of the Hydrogen atoms
• stops at the protonation of the first π bond. 

• turns alkyne into a trans alkene.
• stops at the formation of the alkene. 
• always forms the trans version of the alkyne in the alkene by adding Hydrogen in a anti addition. 

1) O₃

2) Zn, H₂O

+ 

Alkyne

• forms 3 bonds to O, most of the time in a carboxyl formation. 
• If it is a terminal carbon however the fromation will be of a carboxyl and a CO₂

HX with Alkene

(Hydrohalogenation)

• HX with an alkene will for a nonstereospecific bond with H and X adding to either side of the double bond. 
• the H atom will add first to the least subst. carbon in the double bond, because that means that it will form the most stable Carbocation. 
• H-X can go to completion. Aka if there are any more -OH's in the molecule it could get rid of them all.

H₂O, Acid Cat. (H₂SO_4, TsOH, H₃PO₄)

(Hydration) 

• Along the sames lines of the HX addition. 
• H- from the Acid Cat. will add to the least substituted Cabon of the double bond, creating the formation of the carbocation, which will then be attacked by the H₂O.

ROH, Acid Cat. (H₂SO₄, H₃PO₄, TsOH)

Etherfication

• H from the acid cat. will first add to the least subst. side of the double bond then the Oxygen of the ROH will add to the carbocation. 

X₂, CCl₄ to an alkene

(Halogenation)

this will form a "epoxide" like formation where the X atoms have a positive charge. Then the anion of the other X atom will backside attack to break the "Epoxide"

• anti additon of the Cl's

X₂, H₂O + alkene

(Halohydren) 

• forms a anti addition of the X and OH, because there is a X double bond (looking like an epoxide) which has to undergo backsided attack for it to be opened. This causes its anti adition. 
• First bond (X adds) forms the most stable carbocation. 
• H₂O would be analogeous to a basic epoxide opening, where it would open from the most substituted carbon. 

1)Hg(oAc)₂, H₂O + alkene

2) NaBH₄ 

(oxymecration)

• adds the Oxygen to the most substituted carbon. 
• Adds a H atom to the least substituted carbon. which forms the most stable carbocation. 
• could be good for forming an alcohol that then could be switched directly to a alkyl group via PBr₃, or SOCl₂, pyr

1. BH₃
2. H₂O₂, KOH

• adds OH to the least substituted Carbon atom. 
• Is syn addition. 
• adds water to more substitued carbon.

H₂,Pd/C or Pt/C + Alkene

(Hydorgenation)

• adds hydrogen bonds across the double bond
• cis addition
• Will add to all of the multiple bonds, till there are no multiple bonds left. 

1)OsO₄, NMO

2)NaHSO₃,H₂O

or

KMnO₄, H₂O, KOH

(Dihydroxylation)

• Both reagents add OH to the double bond through syn addition

1)9-BBN

2)H₂O₂, KOH

+

Alkene

• more sterically hindered than BH₃, making it more likely to put the OH on the less substituted Carbon of the double bond. 

1. O₃
2. Zn, H₂O

• Breaks the alkene, which will form then two new C O double bonds. 

• reacts with alcohol to make a good -OTs leaving group. 
• pyr will pull hydrogen off of the alcohol when it has the -OHTs⁺ Formation. 

DBU

or

DBN

• These are both good E2 solvents, whenever there is a good leaving group present. 
• OH is not a good Leaving group but -OTs is. 
• E2 happens at 1˚,2˚,3˚ but not Me. 
• Antiperiplaner formation is enforced

• E1 reactions invove a good leaving group and a weaker base. 
• the base shouldnt have a negative sign on it. 
• Happens at 2˚, 3˚, and often competes with Sn1 reactions
• Carbocation rearrangement can occur.
• Very little use because of lack of control.
• Unimolecular reaction, carbocation can form

• E2 reactions occur at 1˚, 2˚ and 3˚ carbocations, that react with a strong base (has a negative charge). 
• DBU, DBN, RO^-, ^-OH
• Anti periplaner conf. between LG and βH 
• Bimolecular reaction means no carbocation is formed.

• is a unimolecular reaction that happens and 2˚, 3˚ alkyl halides when they are reacted with a weak Nuc.
• Carbocartion rearrangement can occur (alkyl or hydride shift.)
• H₂O, ROH, or other non negativly charged atoms react the electrophyle after the LG leaves. 
• Fastest in protic solvent

• can happen at Me, 1˚, and 2˚ (slowest at 2˚, E2 will dominate at 2˚)
• Backside attack and inversion.
• ^-N₃, ^-CN, NH₃, ^-OH, ^-OR, are good for these reactions

• H₂SO₄, TsOH, H₃PO₄ are used to pull off an H and an OH, to form a double bond. 
• Similar to a E1. 
• Carbocation is produced, rearrangement may occur. 
• only non nucleophilic acids can praticicpate in the acidic dehydration 
• E1 happens at 2˚ and 3˚ alcohols
• E2 happens at 1˚ but it is very reactive and unstable. 

Basic Dehydration

POCl₃, Pyr

• Reaction that happens at all alcohols. 
• the POCl₃ attatches to the OH and then the pyr pulls the H off. 
• Acts like a E2 reaction at all alcohols. 
• no carbocation formed. 

• at methyl and 1˚ this reaction acts like a Sn2
• at 2˚ and 3˚ alcohols it acts like Sn1
• H from H-X first protonates the alcohol making it a good leaving group then X^- attacks via Sn2(Backside) or Sn1(enatomers are formed). 

• Can change alcohols to Alkyl's of R-Cl

• Can change alcohols into R-Br via Sn2 at 1˚, 2˚

• Can change aclohols to R-Cl via Sn2 reaction at 1˚ and 2˚. 

• All bonds to the oxygen will be broken if the as the acid protonates them and then further more the X^- will nucleophilicly attack it. 

• Acidic Opening (HOCH₃) will first protonate the Oxygen (H₂SO₄, or acid catalyst) then HOCH₃ will attack the more substituted carbon atom. 
• Basic Opening (^-OCH₃) there will be nucleophilic attack at the least substituted carbon atom and then there is a water work up for the O anion.