Organic Chemistry: Chapter 7, 8, and 9

question

nucleophile
answer

is the pi bond in an alkene an electrophile or nucleophile?
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no
answer

can the alkene be a branch?
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the alkene
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what gets the lowest number when naming an alkene?
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ene
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what does the parent chain name end with for an alkene?
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branches (lowest number)
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if the alkene number is a tie, look at ___________ to decide
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1, 2
answer

alkene is always number ____, the _____ position is always on the other side of the alkene
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tie breakers
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branches are only there to settle _____ ____________
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monosubstituted
monosubstituted
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one non-H
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no
answer

do monosubstituted alkenes have stereoisomers?
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disubstituted
disubstituted
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two non-H
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cis and trans
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how do you differentiate between the stereoisomers of a disubstituted alkene?
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trisubstituted
trisubstituted
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three non-H
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E or Z
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how do you differentiate between the stereoisomers of a trisubstitued alkene?
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atomic weight
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rank the branches of a trisubstitued alkene by ________ __________ to determine hight or low
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E
answer

highs on opposite sides
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Z
answer

highs on the same side
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no, 2 (on each side)
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do you rank all 4 branches of a trisubstituted alkene? if no, how many do you rank?
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different
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assume all R groups are (the same or different) on a trisubstituted alkene
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no, because it may be E or Z but it can not flip to become the other isomer
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do you put the stereoisomer (E or Z) of cyclo-alkenes in the name? if not, why?
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nucleophiles
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are alkenes nucleophiles or electrophiles?
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Markovnikov’s Rule
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a carbocation is most stable when more carbons (or non-hydrogens) are bound to it -carbocations pull e- closer and carbons have more e- than hydrogens
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primary
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carbon bound to one other carbon
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secondary
answer

carbon bound to two other carbons
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tertiary
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carbon bound to three other carbons
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tertiary
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is secondary or tertiary more stable?
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secondary
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is primary or secondary more stable?
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tertiary
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is primary or tertiary more stable?
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hydride shift
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movement of a hydrogen atom with a pair of electrons from one atom to another -a rearrangement that converts carbocations into more stable molecules
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brominium ion
answer

question

trans
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the stereochemisty of a Br2 addition to a cycloalkene is always ________ (cis/trans)
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none
answer

if there is no carbocation, how many rearrangements are there?
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hydrogens
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ignore ______ when naming a molecule cis or trans
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carboxylic acid
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when cleaving an alkene with KMNO4, a monosubstituted half (of the alkene) yields what functional group?
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ketone
answer

when cleaving an alkene with KMNO4, a disubstituted half (of the alkene) yields what functional group?
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CO2
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when cleaving an alkene with KMNO4, a no substituted half (of the alkene) yields what?
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aldehyde
answer

when cleaving an alkene with O3 and Zn, a monosubstituted half (of the alkene) yields what functional group?
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ketone
answer

when cleaving an alkene with O3 and Zn, a disubstituted half (of the alkene) yields what functional group?
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formaldehyde
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when cleaving an alkene with O3 and Zn, a no substituted half (of the alkene) yields what functional group?
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no
answer

when an alkyne reacts with 1 equivalent, is there a mechanism/intermediate?
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1, 2
answer

a triple bond is ____ sigma bond(s) and ____ pi bond(s)
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trans (or E)
answer

when an alkyne reacts with Br2, what is the stereochemistry?
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no
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when an alkyne reacts with H2 and Pt, can you stop it at 1 equivalent (alkene)?
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Lindlar’s catalyst
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what is used in conjunction with H2 to stop an alkyne reaction at the alkene step?
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alkene
answer

when reacting an alkyne in 1 equivalent instead of excess, the reaction stops at the ________ step
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alkane
answer

when reacting an alkyne in excess, the reaction fully reacts to the _______ step
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HBr
answer

what reacts with the alkene during an electrophilic addition
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electrophilic addition
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what is the only reaction with a hydride shift?
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Br2 and H2O (or any halogen X and water)
answer

what reacts with the alkene during a halohydrin reaction?
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OH and Br (or X)
answer

what is added to the final product during a halohydrin reaction?
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Br2 (or any halogen X)
answer

what reacts with the alkene during halogenation?
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Hg(OAc)2, H2O and NaBH4
answer

what reacts with the alkene during oxymercuration?
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OH and H
answer

what is added to the final product during oxymercuration?
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BH3 and H2O2
answer

what reacts with the alkene during hydroboration (NonMarkovnikov)?
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H and OH
answer

what is added to the final product during hydroboration (NonMarkovnikov)?
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OH
answer

during cleavage with KMnO4, Hs turn into _____
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Hs (on the same side)
answer

what is added to the product during hydrogenation?
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H2 and Pt
answer

what reacts with the alkene during hydrogenation?
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hydrogenation
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which is the only mechanism yields a product that is not trans?
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cis
answer

does the reaction of an alkyne with H2 and Lindlar’s catalyst yield a cis or trans product?
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Li, NH3
answer

what do you react with an alkyne to yield trans Hs (hydration)on an alkene?
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HgSO4, H2SO4, H2O
answer

what are the reagents in a hydration (oxymercuration) reaction with an alkyne?
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carboxylic acid and CO2 (no ketone because no disubstituted alkynes)
answer

when cleaving an alkyne, what are the only two functional groups that can result?
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aldehyde
answer

what functional group is in the final product when an alkyne reacts with BH3 and H2O2 (hydroboration)?
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ketone
answer

what functional group is in the final product when an alkyne reacts with HgSO4, H2SO4 and H2O (hydration)?
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no (tautamerizes to ketone)
answer

can the hydration of an alkyne stop at the alkene intermediate?
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no (tautamerizes to aldehyde)
answer

can the hydroboration of a alkyne stop at the alkene intermediate?
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KMnO4, O3 and Zn, or HgSO4, H2SO4 and H2O
answer

what reagents can yield a ketone?
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O3 and Zn, or BH3 and H2O2
answer

what reagents can yield an aldehyde?
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alkene
answer

when naming a molecule that has an alkene and an alkyne with the same number, which wins?
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brominium ion
answer

what is in the intermediate of a halohydrin reaction?

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