Organic reactions of carbox acids
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| What happens when you have a carboxylic acids with a salt? | No REACTION because it already has a negative charge
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| 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-)
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| How would you remember the order of the charged nucleophiles? | Come Now Oliver Over Shore Over Clapping
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| What is capable of reacting with a carboxyllic acid? (Which charged nucleophile(s)? | CH3-, NH2-, OH, SH, -OAc
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| What would the LG be in the above case? | The H would bond with the nucleophiles, leaving the carboxylic O with a negative charge
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| 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
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| Is the same true for salts, though? | Yes
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| 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
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| What are the charged nucleophiles that are capable of carrying out this reaction? What is the LG of this reaction? | All of them "Cl"
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| 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
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| What is the name of the reaction of acyl chlorides with nucleophiles? | Acyl addition elimination (for biochem)
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| What does the reaction of anhydrides and nucleopiles yeild? What is the LG? | Carboxylic acids, LG = "RCOO-"
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| What are the charged nucleophiles that can react with the ESTER? What is the LG?? | CH3- and the NH2- LG is the OR-
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| What are the charged nucleophiles that can react with a primary amide? What is the LG? | CH3- LG is NH2
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| What does the reduction of aldehydes and ketones yeild? | Alcohols
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| What are the reagents required for the carbonyls (aldehydes and ketone) reaction? | NaBH4--Sodium boronhydride and LiALH4, LithiumAluminum Hydride
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| 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
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| What is the second stop of the carbonyl reaction? | dilute acid gives the negatively charged oxygen an H to stabalize the charge
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| 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
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| What is fisher esterfication? | It is when a carb. acid reacts with a weak base to form water and an ester or anhydride
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| FE is to what and Salts are to what? | FE is to weak base and salts are to strong base
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| What is the order of reactivity of addition elimination reactions? IN DECREASING REACTIVITY | Acyl halides, anhydrides, esters and amides
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| What do all derivatives yield upon hydrolysis? | Carboxylic acids
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| What is hydrolysis: | Acid/water or base/water followed by acidification
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| PREPARATION SECTION OF TEST | PREPARATION SECTION OF TEST
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| What is needed for the oxidation of aromatic side chains at the benzyl position? | Strong oxidizing agents like hot HNO3 or KMnO4
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| What solvents are needed for oxidation of primary alcohols? | KMnO4 or CrO3, H2SO Chromic Acid
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| Solvent needed for oxidation of aldehydes? | KMnO4
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| 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
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| What are the solvents needed for carbonation of grignard reagents? | Make grignard reagent by MG metal, add CO2, then acidify with H+
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| Nitrile hydrolysis requires what? | Nitrile is first formed by Sn2 reaction on an alkyl bromide( from alcohols and HBr combination)
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| Second step? | KCN adds
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| Third step? | Water, dilute acid, or water and OH-
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| What's the product? | R COOH
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| What is needed for the hydrolysis of acyl derivatives? | Hydrolysis with water (plus acid or base)
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| Acid chlorides and water give what products? | carb. acid and HCl
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| Anhydrides and water yeild what? | 2 equivalents of carb. acid
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| What do esters need to form carb. acid and alcohol? | Water/acid
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| What is this hydrolysis reaction called in a base? | Saponification
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| What is the last step of saponification? | Forming NEUTRAL acid by acid an acidification step
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| Amides will form RCOOH and an amine with what solvent? | WATER
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| PREPARATION OF CARB ACID DERIVATIVES | PREPARATION OF CARB ACID DERIVATIVES
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| How do you form acid chlorides? What solvents are needed, I mean. | Carb. Acids and Thionyl chloride (SOCL2) and Phosphorus trichloride (PCl3)
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| 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)
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| What solvents are needed to form esters? | Fisher esterfication (Conc. H+, RCOOH, Alcohol), Acid chlorides and an alcohol, Anhydrides an analcohol
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| How will amides form? | Acid chlorides and an amine
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| How will amides and alcohols form? | Esters and an amine
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| How will salts and amides form? | Anhydrides and an amine
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| REDUCTION OF RCOOH AND DERIVATIVES | REDUCTION OF RCOOH AND DERIVATIVES
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| Esters will be reduced, how? | LAH (LiAlH4), followed by acidification yields two equivalents of alcohol
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| How will amides will be reduced | LAH, neutralization with acid yields an amine
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| Nitriles are also known as what? | Cyanides
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| How will nitriles be reduced | LAH, neutrilization with acid forms an amine
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| How else can amines form by reduction? | reduction with H2 and Pt or Pd
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| How will RCOOH be reduced? | LAH, acidification yeilds a primary alcohol
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| 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
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| 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
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| A reaction of an amide with another amide will give? | a fifty-fifty mixture
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| FACTORS AFFECTING BASICITY AND ACIDITY | FACTORS AFFECTING BASICITY AND ACIDITY
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| What are the three factors that impact the acid and base properties? | Hybridization, inductance, resonance
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| What type of hybridization makes a strong base? | SP3, less s character
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| What type of inductance makes a strong base? | lower left hand compounds, less electronegative groups, but additing electron donating group
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| What are electron donating groups? | CH3- and other alkyl groups
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| 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
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| why are amides even worse bases than aromatic amine? | first order equal to second order
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| To have an amide, you need... | a c double bond O must be directy attached to nitrogen
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| What is the acidity of an amid? | very very acidic. PKA 0
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| 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
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