Names And Conditions Of Mechanisms, And Key Definitions Flashcards
What is the name, reagent and conditions for the mechanism from Haloalkane to Alcohol?
Nucleophilic Substitution
Reagent: NaOH
Conditions: Aqueous, heat under reflux
What is the name, reagent and conditions for the mechanism going from Haloalkane to Amine?
Nucleophilic Substitution
Reagent: Excess NH3
Conditions: Ethanol, heat and pressure
What is the name, reagent and conditions for the mechanism going from Haloalkane to Nitrile
Nucleophilic Substitution
Reagent: KCN
Conditions: Water and ethanol
What is the name of the process, reagent and conditions to go from Nitrile to Amine?
Reduction
Reagent: H2 (in the equation; 2H2)
Condition: Nickel (Ni) catalyst
What is the name, catalyst and conditions for the mechanism going from Alcohol to Alkene?
Elimination/Dehydration
Catalyst: Hot concentrated H2SO4
Conditions: Hot
What is the name, reagent and conditions for the mechanism going from Alkene to Alcohol?
Direct Hydration
Reagent: H3PO4
Conditions: Steam
What is the name, reagent and conditions for the mechanism going from Haloalkane to Alkene?
Elimination
Reagent: KOH/NaOH (acts as base, not nucleophile)
Conditions: Ethanol, Reflux
What is the name, reagent and conditions for the mechanism going from Alkene to Haloalkane?
Electrophilic Addition
Reagent: HBr, HCl, Br2, Cl2
Conditions: No conditions required
What is the name and reagent for the mechanism going from Alkene to Alkyl Hydrogen Sulfate?
Electrophilic Addition
Reagent: H2SO4
What is the name of the process of going from Alkyl Hydrogen Sulfate to an Alcohol, and what is the reagent?
Hydrolysis
Reagent: H2O
What is the name, reagent and conditions for the process of going from Alkane to Haloalkane? And what are the names of the steps?
Free Radical Substitution Reagent: Either Br2 or Cl2 Condition: U.V light Steps: Initiation Propagation (two equations) Termination
Define a Nucleophile
An electron pair donor
Define an Electrophile
An electron pair acceptor (AKA a reactive intermediate
Define a Base
A proton acceptor
Define an Acid
A proton donor
What is meant by “More Stable Carbocation”?
The major product has the more stable carbocation. It’s a positive carbon with more carbons around it. E.g a 1° carbocation is less stable than a 2° one.
This is due to the positive inductive effect.
Define the Positive Inductive Effect
The ability to release electron density through a covalent bond
What is the name, reagent and conditions for the mechanism for the Nitration of Benzene (Forms Nitrobenzene)? How is the electrophile/reactive intermediate formed?
How is the Catalyst Re-Formed?
Electrophilic Substitution
Reagent/Conditions: Conc HNO3 and Conc H2SO4 Catalyst
H2SO4 + HNO3 —> HSO4- + H2O + NO2+
HSO4- + H+ —> H2SO4
What is the name, reagent and conditions for the mechanism going from Benzene to Phenylethanone (Friedel-Crafts Acylation)
What is the equation for the formation of the electrophile/reactive intermediate
How is the catalyst Re-Formed?
Electrophilic Substitution
Conditions/Reagents: An acyl chloride e.g RCOCl and an AlCl3 catalyst
RCOCl + AlCl3 —> RCO+ + AlCl4-
(RCO+ = Electrophile)
AlCl4- + H+ —> AlCl3 + HCl
What occurs when forming an Amine from a Haloalkane, if the Haloalkane is also in Excess as well as the NH3?
Further Substitution
Product reacts with Haloalkane to form a 2° anime, and that product reacts to form 3° amine and then that product reacts to form a Quaternary (4°) Ammonium Salt (used in hair conditioner)
What are the Cons to forming an Amine from a Haloalkane for either nucleophilic substitution with excess NH3 (Route 1), or nucleophilic substitution with KCN to form Nitrile, and then reduction with 2H2 and Ni catalyst (Route 2)?
Route 1: Risks Further Substitution
Route 2: KCN is Toxic and also it requires two steps instead of one
What is the name of the process, reagent and conditions for turning the Nitro group (NO2) on Nitrobenzene to an Amine group (NH2)? Give a general equation for the transformation of the alkyl group.
Reduction Reagent: HCl Condition: Tin (Sn) Catalyst NO2 + 6[H] ---> NH2 + 2H2O (NO2 and NH2 are attached to benzene)
What is the risk of reacting HCl with Nitrobenzene to change group to an amine group? And how is this solved?
Risk of product reacting with HCl to form Phenylammonium Chloride
(NH2 group becomes NH3+ with Cl- nearby like when amino acids are in acidic conditions)
Solution:
Add stronger base (NaOH)
NH3+ + Cl- + NaOH —> NH2 + NaCl + H2O
(NH2 and NH3+ are attached to benzene)
What is the name, reagent and conditions for the mechanism going from a Ketone to a 2° Alcohol or an Aldehyde to a 1° Alcohol?
(Reduction)
Nucleophilic Addition
Reagent: NaBH4
(For hydride ion nucleophile :H- )
Condition: Acidic Solvent Needed (For H+ in mechanism)
What is the name, reagent and conditions for the mechanism going from either a Ketone or Aldehyde to a 2° or 1° Hydroxy Nitrile group
(Reduction)
Nucleophilic Addition
Reagent: Potassium Cyanide, KCN, Aqueous and Ethanolic
(Nucleophile: -CN)
Conditions: Acidic Solvent Needed (For H+ in mechanism)
Give the name, conditions and reagent for the 1st method of making esters that you learnt.
Esterification (Reversible via hydrolysis)
Reagent: Carboxylic Acid + Alcohol
Conditions: Concentrated H2SO4 (H+) catalyst and Gentle Heat
(H2O is a side product)
What is Hydrolysis?
The breaking of covalent bonds using water
What are the two methods of Hydrolysis for splitting Esters? And what do both methods form?
Acid-Catalysed Hydrolysis
Reagent: Water
Conditions: Room Temp and Strong Acid Catalyst
Forms: Carboxylic acid and Alcohol
Base-Catalysed Hydrolysis
Reagent: Warm AQUEOUS NaOH
Forms: Salt of the acid (e.g Sodium Propanoate if using ‘something’ Propanoate) and Alcohol
(Once carboxylic acid forms, it reacts with NaOH in an acid base reaction)
What is meant by the term Unsaturated when applied to an Alkene?
Contains a C=C bond
Give the name, reagent and conditions for the mechanism used in the 2nd way if forming Esters you learnt
Addition-Elimination
Reagent: An Alcohol and an Acyl Chloride (RCOCl, all have names ending with ‘Oyl Chloride’)
No specified conditions