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24 Cards in this Set
- Front
- Back
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Alcohols
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- OH group, end in -ol.
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Aromatic ring alcohols
name? |
- ending in phenol.
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Alcohols: Physical Properties
Boiling point? Why higher? acidic or basic? most acidic alcohol? why (hint pKa) |
- Alcohols > hydrocarbons in B.P. (because of H bonding)
- weakly acidic - Phenol most acidic, small pKa. > Strong acids have HIGH Ka's, and SMALL pKa's. |
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Aromatic acidity changes
add e- donating/withdrawing? what happens? |
- adding electron-donating substituents decreases acidity.
adding electron-withdrawing substituents increases acidity. (Resonance) |
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Alcohols: Review
key reaction mechanisms? |
a. Sn1/Sn2 nucleophilic Substitution
b. Electrophilic addition to a double bond c. Nucleophilic addition to a carbonyl |
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Alcohols: Sn1/Sn2 Nucleophilic Substitutions
reactants? |
alkylhalide + OH- >>> Alcohol + halide
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Alcohols: Electrophilic Addition to a double bond
Reactants? products? |
- H20 (water) + alkene >>>> alcohol (syn addition)
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Alcohols: Nucleophilic addition to a carbonyl
Reactants? Products? |
- Grignard reagent (alkylMgBr) + carbonyl >> Alcohol
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Alcohols: Synthesis
4 types |
1. Addition Reactions
2. Substitution Reactions 3. Reduction Reactions 4. Phenol Synthesis |
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Alcohol Synthesis: Addition Reactions
two types |
- Add H20 to double bond
- Organometallic + carbonyl |
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Alcohol Synthesis: Substitution Reactions
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- Sn1/Sn2 reactions of course
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Alcohol Synthesis: Reduction Reactions
what can be reduced to create alcohols? what is needed as a reducing agent? what is the other reducing agent regardless of substrate being reduced? |
- aldehydes, ketones, carboxylic acids, esters.
- LiAlH4 reduces carboxylic acids and esters. - NaBH4 reduces aldehydes and ketones. - Hydronium ion is used also. |
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Alcohol Synthesis: Phenol Synthesis
method? 3 parts reactants? |
- hydrolysis
- diazonium salts > part 1: aminobenzene + Nitric acid/Sulfuric Acid > part 2: diazonium salt + hydronium ion > part 3: phenol product |
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Alcohols: Reactions (From alcohol reagent)
3 types |
- Elimination Reactions
- Substitution Reactions - Oxidation Reactions |
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Alcohol Reagent Reactions: Elimination Reactions
method? reactants? products? what type of elimination? |
- dehydration
- alcohol + sulfuric acid >>> alkene E1 elimination, most substituted alkene favored. |
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Alcohol Reagent Reactions: Substitution Reactions
key concept? conversion types? 5 types products? |
- alcohols can participate in sn1/sn2 reactions, but needs to be better leaving group.
> protonate it (Sn1) > Convert to a tosylate (Sn2) > Form an inorganic ester. (Sn2) > Thionyl chloride -> alkyl chloride > PBr3 -> alkyl bromide |
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Alcohol Reagent Reactions: Oxidation Reactions
what is automatic hint that your dealing with an alcohol oxidation? for primary alcohols? oxidizing agent? > what oxidizing agent takes them "all the way"? for secondary alcohols? super strong oxidant? what is its nickname? how does it affect primary? secondary? |
- when you see a transition metal (Cr or Mn) with lots of oxygen (Cr2O7, CrO3, MnO4) think OXIDATION.
- for primary, PCC is used, converts to ALDEHYDES >KMnO4 takes them to a C.A. - for secondary, PCC or Na/KCr2O7 (in sulfuric acid) creates KETONES - CrO3 (with H2SO4) in acetone (JONES REAGENT). > oxidizes primary alcohols to Carboxylic Acids. > oxidizes secondary alcohols to ketones. |
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Alcohol Reagent Reactions: Oxidation Reactions
Phenol oxidation? what is the product called? oxidizing agent? |
- product is called quinones
- K/Na2Cr2O7 in sulfuric acid |
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Ethers: Nomenclature
two types |
- alkoxyalkanes
> smaller chain as PREFIX > larger chain as SUFFIX - alkyl alkyl ethers. > alphabetical |
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Ethers: Physical Properties
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- low B.P.
- slightly polar and soluble - frequently used as solvents - Do not H-bond. |
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Ethers: Synthesis
nickname? reagents? what other type of alkoxide can be used? what do these reagents mean for the type of reaction? |
- Williamson ether synthesis
- strong nucleophile (alkoxides) and primary alkyl halides. > also can be used with phenols (use strong base) - Sn2 reaction |
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Ether synthesis: Cyclic Ethers
(For Alkanes) >reaction type? >reagents? (For Alkenes) >reaction type? >reagents? |
- internal Sn2 displacement
- Base and H+ - sn2? - peroxy acid (MCPBA) + alkene |
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Ether Reactions: Cleavage
conditions needed? initiation step? reaction mechanism type? |
- high temperature, in the presence of a strong acid (HBr or HI).
- protonation of ether oxygen is initiating step. - goes by Sn1 or Sn2, depending on structures and conditions of ether. |
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Ether reactions: Epoxide Cleavage
what happens when asymmetrical ether attacked? for acid catalyzed? for base catalyzed? |
- highly susceptible to Sn2 reactions
- can use acid or base to cataylze it. >in presence of acid, most substituted attacked >in presence of base,least substituted attacked. |
