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HX
will replace OH with halogen
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H2SO4
make pi bond and remove OH (make most substituted)
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H3PO4
make pi bond and remove OH (make most substituted)
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POCl3
make pi bond and remove OH (primary alcohols)
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SOCl2
replace OH with halogen (Sn2)
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PCl3
replace OH with halogen (Sn2, opposite stereochem)
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XSiR3
will remove H from alcohol and add protecting group
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LiF, acid workup
will remove protecting group
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What makes a good diene?
e- rich groups (e- donating)
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What makes a good dienophile?
e- weak group (e- withdrawing)
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Why are epoxides so reactive?
They have polar bonds and angle strain (bond angles have to decrease to make room for lone pairs)
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HCl, CH3SH
will open epoxide and make OH and add the R group (anti addition)
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What product do you want to make with Diels-Alder reaction?
endo and non-meta product
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Why do dienes favor the s-trans conformation?
sterics
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How do you get a high amount of thermodynamic product?
make sure the reaction is an equilibrium process so you can return to s.mat. and make thermo product favorable
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What is degenerency (MOs)?
MOs of equal energy
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Is blue shift higher or lower energy?
higher energy (shorter wavelength)
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Does energy increase or decrease with more conjugated systems?
energy decreases (pi orbitals get closer together)
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Sulfonate and Et3N
replaces H in OH with sulfonate
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PI3 and LiCN
will replace alcohol with halogen then replace halogen with CN
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What does adding CN straight to a sulfonate do?
replaces sulfonate with CN (get opposite stereochem due to inversion)
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NBS, KOtBu
make a conjugated diene
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SOBr2, Et3N
will replace OH with Br
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NaSCN
will replace halogen with SCN
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KF
will change stereochem of a halogen if protecting group is there
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Br2 on SH
will make into "epoxide", copy s.mat. on other side
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KMnO4 (with no conditions)
make OH into ketone and add OH if H off that C as well as add a sulfonate to SH
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Where does the pi bond go with thermo products?
Between carbons 2 and 3
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