1Alcohols From Alkenes: HX
Markovnikov regioselectivity: more substituted carbocat immediately reacts with H2O, Carbo cat IM possibly rearranges for 3 degree,
Double bond breaks, grabs proton (least sub), carbo cat reacts with water (most sub), Acid deprotonates Water, HA+product
2Alcohols from Alkenes: Hydroboration-Oxidation
Anti markov regio and syn stereo, not carbocation intermediate
Double attacks B of BH3, loses one H to the other carbo cat, same alkene copies over for all H, then all B bonds break and you have 1 of these triples and replace B with OH.
Added syn (so if other substituents, add line for B and H and make dash for subs)
3Alcohols to Alkyl Halides: HX
Sn2 for 1 and 2, sn1 for 3, carbocat might rearrange with strong acid.
H attacks OH, creats H2O+, X- left over attacks, removes water and replaces
4Alcohols to Alkyl Halides: PBR3
HO attacks Lp of P, ejects a Br. Intermediate with H+OPBr2. Pyradine (weak base) deprotonates. Then Br attacks and entire OPBr2 leavong group is seperated
5Alcohols to Alkyl Halides: SOCl2 and pyridine
OH lp attacks s of cl2-s=o, making -O. then =O reforms and cl is expelled. pyradine deprotonates, the Cl attacks removing(o-)s-cl=O
6Conversion of alcohols to sulfonates
OMS/OTS/OTF
O attacks S, reducing 1 double bond. X group leaves, double bond reforms. Removed X deprotonates, boom good lg.
7Cleavage of ethers with dilute HX
Protonate alcohol with H of HX, X attacks this +, then HX attacks again: Hot: 2R-X, Cold: R-X, R-OH [Leave 2/3 degree side first by sn1, IF SP2 C, Leave OH]
8Dehydration of Alcohols
Usually single 1 degree, two 1 degree make mix of ethers. one 1 and one 3 make one ether sn1
O takes the H off of H2So4, then another alcohol attacks, removing the h2o+ and attaching an OH, creating an ether with an extra H. The removed water deprotonates, this creating R-o-R and H3O+.
If you mix 2 alcohols: r1-Oh and R2-OH, you get R1-O-R1, R1-O-R2, R2-O-R2
primary and 3rd, you get : R1-OH and (r2-)(r3-)R4-OH, you get R1-O to R2,R3,R4
9Williamson Ether Synthesis
Oh of NaOH takes the H from the alcohol. Sn2 where O attacks the HX, removes the x, makes product.
If dealing with epoxide (ie cyclohexane, one should be wedge, one dashed, if not cant stereowrk...)
10Epoxidation Formation From Alkenes with peroxy acids
mCPBA! Remember Her.... 3-chloeroperbenzene
Double bond attacks O closest to H and the same time, lone pair of this O attacks the double bond. Bond between this o and next O breaks, forms double bond to closest C. Now C is over loaded, double bond adds 2 e- to last O, but then attack the H, seperating the H from the original O.
cis->cis
trans->trans
Essentially break double bond and put a little triangle on it and for the mCPBA, eseentially collapse the H onto the next closest O
11Epoxide ring opening under acidic and basic conditions
Acid: O attacks proton, then water attacks from more hindered side, breaking the C-O bond on that C and adding OH to other C. Water then deprotonates, 2, 2 OH groups
Base: NUC attacks Less hindered C, breaks C-O bond, water is used to protonate this O, Product
Inversion of Configuration in both cases where R to S or S to R....