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Organic Test 4

Organic reactions of carbox acids

QuestionAnswer
What happens when you have a carboxylic acids with a salt? No REACTION because it already has a negative charge
List, in order of decreasing basicity, the charged nucleophiles that are on the table in the blue sheet. CH3-, NH2-, OH-, OR-, SH-/SR-, -OAc, Cl- (X-)
How would you remember the order of the charged nucleophiles? Come Now Oliver Over Shore Over Clapping
What is capable of reacting with a carboxyllic acid? (Which charged nucleophile(s)? CH3-, NH2-, OH, SH, -OAc
What would the LG be in the above case? The H would bond with the nucleophiles, leaving the carboxylic O with a negative charge
How do you know when you can have a reaction with a charged nucleophile? As long as the LG is MORE stable than the Nucleophile, the reaction WILL happen
Is the same true for salts, though? Yes
What is the product of an acyl halides (carboxyllic with a Cl instead of an O at the far right) with a charged nucleophile? Carboxyllic acid
What are the charged nucleophiles that are capable of carrying out this reaction? What is the LG of this reaction? All of them "Cl"
What first happens to the acyl chloride before the reaction takes place (Before it is attacked with the nucleophile?) It forms a resonance form with a positive charge on the Carbon and negative on oxygen
What is the name of the reaction of acyl chlorides with nucleophiles? Acyl addition elimination (for biochem)
What does the reaction of anhydrides and nucleopiles yeild? What is the LG? Carboxylic acids, LG = "RCOO-"
What are the charged nucleophiles that can react with the ESTER? What is the LG?? CH3- and the NH2- LG is the OR-
What are the charged nucleophiles that can react with a primary amide? What is the LG? CH3- LG is NH2
What does the reduction of aldehydes and ketones yeild? Alcohols
What are the reagents required for the carbonyls (aldehydes and ketone) reaction? NaBH4--Sodium boronhydride and LiALH4, LithiumAluminum Hydride
What is the first steop of the carbonyl reaction? The reagent gives a hydride to the central carbon atom, giving the oxygen a negative charge
What is the second stop of the carbonyl reaction? dilute acid gives the negatively charged oxygen an H to stabalize the charge
What is the only functional group capable of reacting with a carboxyllic acid to form a salt? strong base neutral nucleophiles can react to form a salt (O of carb. acid has a negative charge
What is fisher esterfication? It is when a carb. acid reacts with a weak base to form water and an ester or anhydride
FE is to what and Salts are to what? FE is to weak base and salts are to strong base
What is the order of reactivity of addition elimination reactions? IN DECREASING REACTIVITY Acyl halides, anhydrides, esters and amides
What do all derivatives yield upon hydrolysis? Carboxylic acids
What is hydrolysis: Acid/water or base/water followed by acidification
PREPARATION SECTION OF TEST PREPARATION SECTION OF TEST
What is needed for the oxidation of aromatic side chains at the benzyl position? Strong oxidizing agents like hot HNO3 or KMnO4
What solvents are needed for oxidation of primary alcohols? KMnO4 or CrO3, H2SO Chromic Acid
Solvent needed for oxidation of aldehydes? KMnO4
How do you know what the product of the preparation of acids is? It is usually the main compuund, like a benzene ring minus its attachments, but instead of its old attachments, it has the COOH
What are the solvents needed for carbonation of grignard reagents? Make grignard reagent by MG metal, add CO2, then acidify with H+
Nitrile hydrolysis requires what? Nitrile is first formed by Sn2 reaction on an alkyl bromide( from alcohols and HBr combination)
Second step? KCN adds
Third step? Water, dilute acid, or water and OH-
What's the product? R COOH
What is needed for the hydrolysis of acyl derivatives? Hydrolysis with water (plus acid or base)
Acid chlorides and water give what products? carb. acid and HCl
Anhydrides and water yeild what? 2 equivalents of carb. acid
What do esters need to form carb. acid and alcohol? Water/acid
What is this hydrolysis reaction called in a base? Saponification
What is the last step of saponification? Forming NEUTRAL acid by acid an acidification step
Amides will form RCOOH and an amine with what solvent? WATER
PREPARATION OF CARB ACID DERIVATIVES PREPARATION OF CARB ACID DERIVATIVES
How do you form acid chlorides? What solvents are needed, I mean. Carb. Acids and Thionyl chloride (SOCL2) and Phosphorus trichloride (PCl3)
What solvents are needed to form anhydrides? Pyridine (with acid chlorides and carb. acids or RCOOH salt) or Heat (with carb. acids and loss of water)
What solvents are needed to form esters? Fisher esterfication (Conc. H+, RCOOH, Alcohol), Acid chlorides and an alcohol, Anhydrides an analcohol
How will amides form? Acid chlorides and an amine
How will amides and alcohols form? Esters and an amine
How will salts and amides form? Anhydrides and an amine
REDUCTION OF RCOOH AND DERIVATIVES REDUCTION OF RCOOH AND DERIVATIVES
Esters will be reduced, how? LAH (LiAlH4), followed by acidification yields two equivalents of alcohol
How will amides will be reduced LAH, neutralization with acid yields an amine
Nitriles are also known as what? Cyanides
How will nitriles be reduced LAH, neutrilization with acid forms an amine
How else can amines form by reduction? reduction with H2 and Pt or Pd
How will RCOOH be reduced? LAH, acidification yeilds a primary alcohol
How will all reactions with neutral nucleophiles (Except for what) work? Except for with amides, all other functional groups, the LG will be the larger group, it will look like a grignard reaction, the LG will be the largest molecules connected together
What will the amide reaction with netural nucleophile Water look like? You will get an NH4 and salt because it's an acid-base reaction
A reaction of an amide with another amide will give? a fifty-fifty mixture
FACTORS AFFECTING BASICITY AND ACIDITY FACTORS AFFECTING BASICITY AND ACIDITY
What are the three factors that impact the acid and base properties? Hybridization, inductance, resonance
What type of hybridization makes a strong base? SP3, less s character
What type of inductance makes a strong base? lower left hand compounds, less electronegative groups, but additing electron donating group
What are electron donating groups? CH3- and other alkyl groups
What affect does resonance have on amines? Aromatic amines have resonance forms and their resonance forms spread electrons around ring, amking e- less available to react=weaker base
why are amides even worse bases than aromatic amine? first order equal to second order
To have an amide, you need... a c double bond O must be directy attached to nitrogen
What is the acidity of an amid? very very acidic. PKA 0
What are the steps of saponification? First, get resonance intermediate by moving double bond, then have nucleophile attack, then get rid of negative charge on O and have leaving group leave, then have the LG grab the H on the molecule....the last step is getting rid of the negative charge
Created by: talkglitter2486