ochem reactions flashcards

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11 Terms

1
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naming alkenes

double carbon bond always starts with 1

Count based on the lowest starting numbers for significant substituents (priority based on atomic number)

end -ene

2
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regiochemistry (markovnikov’s rule)

the non-h group adds to the more substituted carbon in the alkene

<p>the non-h group adds to the more substituted carbon in the alkene</p>
3
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syn addition (stereospecific)

2 atoms or groups are added to the same side

<p>2 atoms or groups are added to the same side</p>
4
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anti addition (stereospecific)

2 new atoms/groups added to opposite side

<p>2 new atoms/groups added to opposite side</p>
5
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Elimination reactions with alcohols (rehydration reaction)

forms a water molecule, secondary and tertiary molecules may contain rearrangements (and thus, contain carbocations in mechanism)

usually H2SO4 or [H+] reactants

removal of alcohols with acids to make alkenes

<p>forms a water molecule, secondary and tertiary molecules may contain rearrangements (and thus, contain carbocations in mechanism)</p><p>usually H2SO4 or [H+] reactants</p><p>removal of alcohols with acids to make alkenes</p>
6
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Direct elimination of alcohols using POCl3

(1, 2, 3 alcohols) this will ALWAYS be E2 NO CARBOCATION INTERMEDIATE

POCl3 reactant, and Py (pyridine) is usually a solvent

Zaitsev products used, can have multiple major products

removal of alcohol with E2

<p>(1, 2, 3 alcohols) this will ALWAYS be E2 NO CARBOCATION INTERMEDIATE</p><p>POCl3 reactant, and Py (pyridine) is usually a solvent</p><p>Zaitsev products used, can have multiple major products </p><p>removal of alcohol with E2</p>
7
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Hydrohalogenation

adding H and X (Cl, Br, I)

regioselective! X adds to more substituted carbon based upon the Markovnikov’s rule

watch for H- or CH3- shifts to most stable rearrangement

product is nonstereoselective, making a racemic mixture with diastereomers/enantiomers

<p>adding H and X (Cl, Br, I)</p><p>regioselective! X adds to more substituted carbon based upon the Markovnikov’s rule</p><p>watch for H- or CH3- shifts to most stable rearrangement</p><p>product is nonstereoselective, making a racemic mixture with diastereomers/enantiomers</p>
8
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acid catalyzed hydration

adding H and OH, OPPOSITE of dehydration reactions

uses dilute H2SO4 in H2O, or H3O+, or the addition of an [H+] catalyst, use alcohols to make ethers

H+ and methyl shifts!! creates a carbocation intermediate

regioselective, according to Markovnikov’s rule (more substituted c)

nonspecific racemic mixture

<p>adding H and OH, OPPOSITE of dehydration reactions</p><p>uses dilute H2SO4 in H2O, or H3O+, or the addition of an [H+] catalyst, use alcohols to make ethers</p><p>H+ and methyl shifts!! creates a carbocation intermediate</p><p>regioselective, according to Markovnikov’s rule (more substituted c)</p><p>nonspecific racemic mixture</p>
9
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oxymercuration-demercuration

mechanism is NOT on the exam

two step, with stereoisomers

adds H and OH, with an end result of alcohol with water

does NOT form a carbocation; no methyl or hydride shifts

Markovnikov’s rule even though no h/ch3 shifts

<p>mechanism is NOT on the exam</p><p>two step, with stereoisomers</p><p>adds H and OH, with an end result of alcohol with water</p><p>does NOT form a carbocation; no methyl or hydride shifts</p><p>Markovnikov’s rule even though no h/ch3 shifts</p>
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hydroboration oxidation

mechanism NOT on exam

ANTImarkovnikov reaction of OH/alcohol, to less substituted carbon

2 step with NO C+ intermediate, and NO shifts

NONstereospecific

<p>mechanism NOT on exam </p><p>ANTImarkovnikov reaction of OH/alcohol, to less substituted carbon</p><p>2 step with NO C+ intermediate, and NO shifts</p><p>NONstereospecific</p>
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halogenation

adds 2X (x= Cl, Br, I)

NO C+ intermediates; no shifts

No markovnikov addition; anti addition and stereospecific (X will add opposite to each other, bc more room behind the X bc halogens are big/bulky)

<p>adds 2X (x= Cl, Br, I)</p><p>NO C+ intermediates; no shifts</p><p>No markovnikov addition; anti addition and stereospecific (X will add opposite to each other, bc more room behind the X bc halogens are big/bulky)</p>