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Definitions |
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primary alcohos----- ? ----carboxylic acids
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aldehydes
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___________ will not reduce carbox ac and esters to alcoh
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NaBH4
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why do you only need mild react condit?
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bec the phenol is more acidic
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ether is
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2 alkyl or aryl gr bonded to an oxy
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second alcohols---- ?
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ketons
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by protonating an alcohol you make it?
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a good leav gr
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ROR is a?
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ether
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this process of getting rid of the alcoh is called?
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dehydration
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SOCl2 is?
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thionyl chloride
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when you see these, think of?
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oxidation
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primary alcohols to aldehyde is done w?
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PCC
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diethyl ether can be used as ?
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medical anesthetic
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the substrate cant be highly substituted but the attacking alkoxide?
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can be highly substituted
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NaBH4 is?
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sodium borohydride
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whats the disadvant?
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it will destroy most funct gr other than the phenol gr and its alkylated deriv
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ROH are
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alcohols
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alcoh can be made by reducing?
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aldehydes, ketones, carboxylic acids, esters
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alcohols are usually dehydrated with ?
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H2SO4
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the hydroxyl gr of _________ are more acidic than alcohols
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phenols
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__________ will reduce carboxy ac and esters to alcoh
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LAH
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electr donating gr ______________ the alkoxide anion
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destabl
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oxirane is also called?
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epoxide
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who is more oxidized an aldehye or a carboxylic acid?
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carboxylic acid
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smaller chain is?
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alkoxy
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epoxides easily undergo what kind of react?
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Sn2
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metal alkoxides act as?
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nucleophiles
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solub in water?
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only slightly sol
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phenols undergo electr aromatic?
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substit react. it has lone pairs it can donate to the ring
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since its SN2 you need?
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a strong nucleophile (like alkoxide)
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makes?
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an alkyl halide and an alcohol
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the mech of dehydration of an alcoho is?
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E1
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ethers react w O2 to form?
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peroxides
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strong acids have ___________ Ka's
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high
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ether will bec ?
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it will split and end up as 2 alkyl halides
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phenols plus oxidizing reagents will make?
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quinones.
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because the -OH gr has high priority, its carbon must be?
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in the carbon backbone with the low numb poss
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aldehydes, ketones, carbox ac, esters can be red to?
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alcohols
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which is more selective?
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NaBH4
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this is a ?
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nucleophilic substition
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why do epoxides easily undergo SN2 react?
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bec they are highly strained
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bp of alcohols are signif are higher than alkanes bec?
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hydrogen bonding
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-OH is?
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hyroxyl group
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oxacyclopentane is also called?
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tetrahydrofuran
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second alcohol plus Na2Cr2O7/H2SO4 will make a
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ketone
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oxid of alcohols usually is done with?
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some form of chromium (VI)
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smaller rings have more _____________, making them less stable
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angle strain
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what reagent do you need to cleave an ether?
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high temp, HBr, HI
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to make a cyclic ether, the _________ and the __________ are part of the same molecule
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nucleophile
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name 3 cyclic ethers?
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oxirane
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b.base catalyzed
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a. acid
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ethers are named as?
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alkoxyalkanes
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when you see a transition metal like Cr or Mn with lots of oxy think of?
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oxidation
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LAH is?
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lithium aluminum hydride
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common name would be?
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ethyl methyl ether
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hydrolysis of a diazonium salt will turn an aromatic NH2 gr into a?
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OH group
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C5H6NCrO3Cl is ?
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PCC
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__________ stabilize the alkoxy anion, mak the alcoh more acidic
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electr withdraw
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which carbon is nuclephilically attack? in pres of acid?
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the more subst c
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hydrolysis of diazonium uses what reagants?
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HNO2/HSO4 followed by H3O
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methanol is _________ alcohol
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wood
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thionyl chloride is?
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SOCl2
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more bonds to ________ means more oxidized
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oxygen
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phenols can _______ with inorganic bases like NaOh
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form salts
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ROOR is the formula for?
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peroxides
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what will be the maj one?
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the more stable alkene. occurs thr movement of a proton to prod the more stable second carbocat
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ethanol can also be called?
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ethyl alcohol
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CrO3/H2SO4/acetone is __________ reagent
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Jones reagent
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ethers do hydrogen bonding
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f. they dont have hydrog attach to O
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Thionyl chloride is used to?
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make an alcohol into an inorg ester and then an alkyl halide
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you change the alc to a?
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inorganic ester. which will then do SN2
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how do you make phenols?
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with arylsulfonic ac and hot NaOH
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is started by?
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protonation of ether oxygen
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alcohol plus PCC will make?
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aldehyde
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PCC and also ___________ can both be used to make second alcholos
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alkali dichromate salt
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what are the 3 big mech for alcohols?
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1. Sn1, Sn2 nucl subst
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alcohol can be thought of as a subst ____________
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water molecule
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to displace a OH gr you have to?
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make it a good leaving gr by protonating it to make H2O
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general formula for an ether is?
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ROR
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methanol can be made by destruct distillation of?
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wood
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which c is nucl att?
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the least subs c
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are ?
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similar to alkanes
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alcohol + sodium dichromate salt ----->
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carboxy acid
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displac of hydroxy gr in subst react is rare bec?
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hydrox ion is a poor leav gr
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primary alc + CrO3/H2SO4/acetone --->
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carboxy acid
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what 3 ways can you turn an alchol into a good leav gr for an Sn1/Sn2 react?
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1. protonate it
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strong acids have _________ pKas
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small
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alcohol + PCC will not overoxidize to?
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an carboxylic acid
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PCC can make secod alc into?
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ketones
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can also be used w phenols
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t
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cleavage of straight chain ehters needs?
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vigorious condit
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you can think of ether as being a disubstituted ?
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water molec
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aloohols can form from _____________ to a double bond
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electrophilic addit to a double bond
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alcohols can be prep via?
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1. addit of water to double bonds
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the more hydroxy gr a molec has the more ?
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hydrogen bonding
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whats a better way of making phenols than by using arylsulfonic acids with hot NaOH?
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hydrolysis of diazonium
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larger chain?
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is named as suffix
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second alcholo +CrO3/H2SO4/acetone --->
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ketone
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ArOH is called?
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phenol
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PCC versus KMnO4
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KMno4 will oxid to carboxy acid
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MCPBA stands for?
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m-chloroperoxybenzoic acid
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alcohols are ?
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ol
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methanol is toxic and can cause?
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blindness
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PCC will make what from an alcholo?
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aldehyde
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metal alkoxides w prim alkyl halides or tosylate will make?
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ethers
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Na2Cr2O7 is?
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sodium dichromate salt
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mcpba is a?
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peroxy acid
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hydrogen bonds form on the "phone" the "fon" means?
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h with F, O, or N will make hydrogen bonds
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acidity ____________ as more alkyl gr are attached
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decre
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PCC is
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pyridium chlorochromate
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a protonated alcohol is good for a _____________ react
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Sn1
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RCOOOH is a?
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peroxy acid
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OH gr is __________, ___________ direct ring const
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strongly activating
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oxidat of an alkene with _________ will produce a oxirane
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peroxy acid like mcpba
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alcohols are weakly?
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acidic
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which is more powerful and diff to work with?
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LAH
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cleavage of cyclic ethers can be acid or base catalyzed
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t
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why is this favored?
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bec the nucleoph and leaving gr are foced into high conc w each other bec they are on the same molec
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E1 you want to form the most stable?
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carbocation
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makes ethers from?
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metal alkoxides w prim alkyl halides or tosylates
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to make an alc into a alkyl bromide you react alc w?
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PBr3
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the hydroxy gr of phenols are more acidic than alcohols due to ?
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resonance struct that distr negat ch thr the ring.
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acts via a ___________ mechanism
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SN2
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epoxide SN2 react can be catalyzed by ________ or _____________
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acid or base
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what kind of gr make the alcohol more acidic?
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electr withdraw
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alkene + mcpba will make?
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an oxirane
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cyclic ethers are prepared via ______________ mechanism
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Sn2 internal displacement
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ethers + ? will form peroxides
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O2
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why do you need to protonate the ether oxy?
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bec otherwise the leaving gr is alkoxide which is strongly basic and a bad leav gr
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alcohol conv to tosylate (p-toluenesulfonate) gr is a good leav gr for a ___________ react
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Sn2
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an alcohol can form from a __________ to a carbonyl
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nucleoph addit
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why does acidity decr as more alkyl gr are added to an alcohol?
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bec electr donat alkyl gr destab the alkoxide anion
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phenols are good subst for electr aromatic subst
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t
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alcohols plus what will make an intermed inorgan ester and HCL?
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thionyl chloride
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Common naming of ethers use?
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alkyl alkyl ethers
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an alcoh can be made into an alkene suing?
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a strong acidic solution
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Jones reagent is?
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CrO3/H2SO4/acetone
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to reduc aldeh, ketones, carb acids, esters to alcoh you use?
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LiAlH4, LAH,
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