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79 Cards in this Set
- Front
- Back
ethylene
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ethene
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methylene group
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=CH2 substituent
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vinyl group
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H2C=CH- substituent
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allyl group
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H2C=CHCH2- substituent
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propylene
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propene
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isobutylene
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2-methylpropene
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isoprene
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2-methyl-1,3-butadiene
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hyperconjugation
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an electronic interaction that results from overlap of a vacant p orbital on one atom with a neighboring C-H sigma bond. results when alkenes are substituted.
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regiospecific
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only one of two possible orientations of addition occurs
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Markovnikov's rule
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in the addition of HX to an alkene, the H adds to the carbon with fewer alkyl substituents and the X attaches to the carbon with more alkyl substituents
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Hammond postulate
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states that we can get a picture of what a transition state looks like by looking at the structure of the nearest stable species. exergonic reactions have transition states that resemble reactant; endergonic reactions have transition states that resemble product
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hydride shift
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the shift of a hydrogen atom and its electron pair (a hydride ion, H-) between neighboring carbons
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hypohalous acid
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any oxyacid of a halogen of general formula HOX
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epoxide
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three-membered cyclic ether
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diol
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two -OH groups
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halohydrin
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OH and X
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dehydrohalogenation
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the loss of HX from an alkyl halide
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dehydration
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the loss of water from an alcohol
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halogenation
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addition of bromine or chlorine to alkenes to produce dihalides
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halogenation of alkenes always results in cis/trans
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trans
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anti stereochemistry
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adds on opposite faces of double bond
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bromonium/chloronium ion
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R2Br+ or R2Cl2, intermediate formed in halogenation of alkenes, looks like a triangle
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NBS/DMSO results in
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halohydrin
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X2/H2O results in
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halohydrin
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hydration
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when water adds to alkenes to form alcohols
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protonated alcohol
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has -H2O+
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oxymercuration/demercuration 2 steps
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1. Hg(OAc)2, H2O/THF
2. NaBH4 |
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oxymercuration/demercuration results in
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an alcohol
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mercurinium ion is the intermediate in
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demercuration
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in oxymercuration, the -OH attaches to the
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more highly substituted carbon (Markovinikov)
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the second intermediate in oxymercuration/demercuration
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an organomercury compound (-OH and -Hg(OAc) on opposite sides of what used to be double bond)
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used for demercuration
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NaBH4
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hydroboration
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addition of B-H bond in BH3 in THF solvent to alkene
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hydroboration results in
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organoborane intermediate, BH2 and H added to alkene
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what follows hydroboration
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oxidation with H2O2 in a basic solution which yields an alcohol
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hydroboration is Markovnikov or non
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non-Markovnikov
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BH3-THF reacts with alkenes to form
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trialkylboranes
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boron and hydrogen add to alkene with ___ stereochemistry
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syn
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boron (and eventually -OH) adds to the more/less highly substituted carbon
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less
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H2 with a palladium or platinum catalyst is used to
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hydrogenate alkenes
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reduction
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a reaction that results in a gain of electron density by carbon
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hydrogenation usually occurs with ___ stereochemistry
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syn
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oxidation
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a reaction that results in a loss of electron density by carbon
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peroxyacid
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RCO3H
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peroxyacids transfer . . .
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an oxygen to an alkene to make an epoxide
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epoxides can be synthesized with
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halohydrins in water and a base, like Cl2/H2O and NaOH/H2O
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glycol
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dialcohol/diol
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epoxides undergo an acid-catalyzed reaction to give a
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diol
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net result of alkene epoxidation/hydrolysis
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hydroxylation
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hydroxylation
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addition of an -OH group to each of the carbons on either side of the =
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epoxidation/hydrolysis results in cis or trans
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trans
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hydroxylation can occur without the intermediate epoxide by treating the alkene with
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osmium tetroxide, OsO4
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OsO4 results in ____
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syn addition of two -OH groups
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osmate
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intermediate in OsO4/pyridine reaction
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cyclic osmate is cleaved by using
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NaHSO3/H2O
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often used in OsO4 reactions
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NMO
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molozonide, which rearranges to form ozonide
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intermediate in ozone reaction with alkene
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ozonolysis happens with
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O3/CH2Cl2
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after ozonolysis, reduction occurs thru
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a reducing agent like Zn/CH3CO2H,H2O
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net result of ozonolysis/reduction
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two carbonyl compounds
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ketone
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R(C=O)R'
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aldehyde
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R-CHO
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phenol
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ring with C6H5 bonded to hydroxyl group
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also used for cleavage of double bonds to form carbonyl compounds
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KMnO4/H3O+
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alkenes can be cleaved following hydroxylation by
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periodic acid, HIO4, in H2O, THF
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carbene
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R2C with one lone pair
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stereospecific
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only one stereoisomer is formed as a product
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Simmons-Smith reaction
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CH2I2 + Zn(Cu) ->ICH2-ZnI
which will add the CH2 to an alkene, making cyclopropane |
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carbenoid
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a metal-complexed reagent like Zn(Cu) that acts like a carbene
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3 steps of polymerization
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initiation, propagation, termination
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vinyl monomers
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substituted ethylenes
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acetylene
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the simplest alkyne
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enynes
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compounds with both double and triple bonds
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alkynes can be prepared by treatment of an dihaloalkane with
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a strong base like KOH
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HX addition to an alkyne (in excess) is usually cis/trans
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trans
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Br2 and Cl2 add to alkynes to form cis/trans alkenes
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trans
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enol
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vinylic alcohol
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tautomers
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like enol and the ketone in the hydration of an alkyne, they switch on their own
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alkynes are converted to enols and then ketones with
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H2O, H2SO4/HgSO4
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