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Organic Test 4
Organic reactions of carbox acids
| Question | Answer |
|---|---|
| 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
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