REACTIONS Flashcards by Jenine S

Draw out the mechanism for halohydrin formation

refer to notes

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product of dihydroxylation

vicinal diols aka glycol (alcohol attachments on adjacent carbons)

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What factor determines the rate of SN1 reactions?

electronics- the stability of the carbocation

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hydroboration/oxidation of alkynes is markov? non markov?

non markovnikov

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What happens to stereochemistry in an SN1 reaction?

stereochemistry is lost (since there’s a 50-50 chance of the Nu attaching to a particular side) and so you must draw both enantiomers or indicate that the product is a racemic mixture

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reagents of free radical halogenation of alkanes

Br₂or Cl₂ and heat or light

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product of dissolving metal reduction

alkene

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reagents of catalytic hydrogenation with lindlar’s catalyst

Pd poisoned with Pb

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halogenation of alkynes results in syn? anti?

anti

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Draw out the mechanism for hydroboration/oxidation of alkynes

refer to notess

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What happens to stereochemistry in an SN2 reaction?

stereochemistry is inverted

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What factor largely determines the rate of SN2 reactions?

steric hindrance

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product of hydrohalogenation of alkenes

haloalkane

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products of acid-catalyzed hydration of alkynes

enol and ketone

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What reaction is acid-catalyzed hydration of alkynes analogous to?

oxymercuration of alkenes

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Are 3° haloalkanes are more likely to react by SN1 or SN2? YYY

SN1; 3° haloalkanes make very stable carbocations and are protected from backside attack, preventing SN2

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What 3 reactions form haloalkanes (an alkane with one halogen attachment)?

hydrohalogenation of alkenes, HBR addition to alkenes under radical conditions, and free radical halogenation of alkanes

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intermediate of allylic bromination

allyl radical

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product of catalytic hydrogentation with lindlar’s catalyst

alkene

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Draw out the mechanism for oxymercuration/reduction.

refer to notes

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Oxymercuration/reduction results in anti? syn? addition

anti

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Which of the 3 reactions that form alcohols is carbocation rearrangement/1,2 hydride shifts possible?

acid-catalyzed hydration of alkenes

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What happens in an SN2 reaction?

Nu attacks from the backside; bond between carbon and Lv breaks and bond between carbon and Nu forms at the same time

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hydroboration/oxidation is Markov? non Markov?

non non non nan nan nan nan

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halogenation of alkenes results in syn? anti?

anti

intermediate of halogenation of alkynes

bridged halogen ion

intermediate of oxymercuration/reduction

bridged mercurinium ion

Draw the transition state of an SN2 reaction.

refer to notes

Draw out the mechanism of acid-catalyzed hydration of alkynes

refer to notes

product of acid-catalyzed hydration of alkenes

alcohols

products of hydroboration/oxidation of alkynes

internal alkynes: ketone and enol terminal alkynes: aldehyde and enol

Why is an SN2 reaction called so?

because both the Nu and the Lv ae involved in the rate determining step

List carbocations from least stable to most stable (for SN1 considerations)

methyl \< 1° alkyl \< 2° alkyl, 1° allylic, 1° benzylic \< 3° alkyl, 2° allylic, 2° benzylic \< 3° allylic, 3°benzylic

reagents of oxymercuration/reduction

1. Hg(OAc)₂, H₂O 2. NaBH₄

intermeidate in halogenation of alkenes

bridged halogen ion

reagents of allylic bromination

NBS, light

reagents of hydroboration/oxidation of alkynes

1. BH₃, THF (or (sia)₂BH if you just want one hydroboration step) 2. H₂O₂, NaOH

product(s) of oxymercuration/reduction

alcohols

Which of the 3 reactions that form alcohols is non-Markovnikov?

hydroboration/oxidation of alkenes

Free radical halogenation of alkanes is regioselective in the order ___ and ___ is more regioselective than \_\_\_.

3°\>2°\>1° chlorine bromine

Draw out the mechanism for free radical halogenation of alkanes

refer to notes

intermediate of hydrohalogenation of alkynes

vinylic carbocation (positive charge on one of the carbons of a carbon-carbon double bond)

reagents of ozonolysis

1. O₃ 2. (CH₃)₂S aka DMS

Oxymercuration/reduction is markov?antimarkov?

markov

product of catalytic hydrogenation of alkenes and alkynes

alkanes

What 3 reactions form aldehydes and ketones?

ozonolysis, acid-catalyzed hydration of alkynes, and hydroboration/oxidation of alkynes

acid-catalyzed hydration is Markov or non-Markov?

Markovnikov

What 3 reactions form alcohols?

hydroboration/oxidation of alkenes, acid-catalyzed hydration of alkenes, oxymercuration/reduction

catalytic hydrogenation with linlar catalst results in syn? anti? addition

syn

Draw out the mechanism for hydrohalogenation of alkenes

refer to notes

product of hydrohalogenation of alkynes

haloalkene with halogen on more substituted carbon geminal dihaloalkane, with 2 halogen atoms on the most substituted carbon

draw out the mechanism for dissolving metal reduction

refer to the book cuz you never wrote it down

Draw out the mechanism for dihydroxylation

refer to notes

product of halogenation of alkynes

1 mole of molecular halogen = vicinal dihaloalkene 2 moles of molecular halogen = vicinal tetrahaloalkane

In halohydrin formation, OH goes on the ___ carbon, and X₂ goes on the ___ carbon.

more substituted

What are the 2 ways to form alkenes?

dissolving metal reduction, catalytic hydrogenation with lindlar catalyst

dihydroxylation results in syn? anti?

syn

reagents of acid-catalyzed hydration of alkenes

H₂O and H₂SO₄

reagents of hydroboration/oxidaation

1. BH₃ 2. H₂O₂, NaOH

intermediate that forms in acid-catalyzed hydration of alkenes

carbocation

dissolving metal reduction results in syn? anti? addition

anti additon of hydrogens

reagents of acid-catalyzed hydration of alkynes

H₂O, H₂SO₄, HgSO₄

What are the 2 reactions that form alkynes?

alkylation of acetylide anions, dehydrohalogenation

reagents of dissolving metal reduction

2Na NH₃

reagents of hydrohalogenation of alkynes

2 mol HBr

intermediate of hydrohalogenation of alkenes

carbocation intermediate; rearrangements are possible

product of halogenation of alkenes

vicinal dihaloalkanes

hydroboration/oxidation of alkynes results in syn? anti?

syn

halohydrin formation results in syn? anti? addition

anti addition

reagents of halogenation of alkenes

X₂, CH₂Cl₂

Draw out the mechanism for ozonolysis

refer to notes

Draw out the mechanism of acid-catalyzed hydration of alkenes.

refer to notes

Draw out the mechanism for the hydrohalogenation of alkynes

refer to notes

hydrohalogenation of alkynes is markov? non markov?

Markovnikov

product of free radical halogenation of alkanes

haloalkanes

Which of the 3 reactions that form alcohols is Markovnikov?

acid-catalyzed hydration of alkenes, oxymercuration/reduction

Which of the 3 reactions that form alcohols forms a racemic mixture?

hydroboration/oxidation of alkenes, oxymercuration/reduction

acid-catalyzed hydration of terminal alkynes is markov? anti markov?

markovnikov

product of ozonolysis

carbon-carbon double bond is cleaved and an oxygen bandaid is put on each wound

intermediates of acid-catalyzed hydration of alkynes

bridged mercurinium ion

Catalytic hydrogenation results in syn? anti? addition

syn

reagents of halogenation of alkynes

2 mol X₂, CH₂Cl₂

intermediates of ozonolysis

molozonoide, which rearranges to ozonoide

Draw out the mechanism for allylic bromination.

refer to notesss

product of hydroboration/oxidation of alkenes

alcohols

Why is an SN1 reaction called so?

because only 1 species- the haloalkane- is involved in the rate determining step

Draw out the mechansim for hydroboration/oxidation of alkenes.

refer to notes

reagents of halohydrin formation

X₂, H₂O

draw out the mechanism for the halogenation of alkynes

refer to notes

reagents of hydrohalogenation of alkenes

hydrohalogenation of alkenes is markov? or non-markov?

markovnikov

hydroboration/oxidation results in syn? anti? addition

syn, since C-B and C-H bonds form simultaneously

reagents of dihydroxylation

1. OsO₄ 2. NaHSO₃/H₂O

reagents of catalytic hydrogenation of alkenes and alkynes

H₂ Pd, Pt, Ni, some metal catalyst 2 mol of H₂ if starting from an alkyne

What happens in an SN1 reaction?

bond between C and Lv is broken completely carbocation intermediate is formed and molecule becomes trigonal planar Nu attacks from either side racemic mixture is formed

Draw out the mechanism for halogenation of alkenes

refer to notes

intermediate of halohydrin formation

bridged halogen ion