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Organic Chemistry 1 > Reactions/Mechanisms > Flashcards

Reactions/Mechanisms Flashcards

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1
Q

Sn2

A

intermediate: none (concerted mechanism)
nucleophile: strong
solvent: aprotic (ex: DMSO)
stereochemistry: inverted
preference: methyl or first degree NaN3, NaCN, NaI, NaBr, NaSH, NaSr)

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2
Q

E2

A

intermediate: none (concerted mechanism)
base: strong (LDA or (CH3)3CONa
preference: 3rd degree
stereochemistry: anticoplanar hydrogen
solvent: protic or aprotic
markovnikov

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3
Q

SN1

A

intermediate: carbocation
nucleophile: weak
solvent: protic
preference: 3 degree

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4
Q

E1

A

intermediate: carbocation
base: weak (CH3)COH
solvent: pprotic
LG Preference: 3rd degree
markovnikov

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5
Q

Bromination

A

reaction type: alkane
intermediate: radical
regioselectivity: Markovnikov
stereoselectivity: none
products: 1 bromine on more substituted side
reactants: Br2 and light

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6
Q

Chlorination

A

reaction type: alkane
intermediate: radical
regioselectivity: none
stereoselectivity: none
products: 1 chlorine on most stable position
reactants: Cl2 and light

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7
Q

Addition of Hydrogen Halides

A

reaction type: alkene
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: haloalkene with bromine on more sub. side
reactants: HBr

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8
Q

Radical Autoxidation

A

reaction type: alkene
intermediate: radical
regioselectivity: antimarkovnikov
stereoselectivity: none
products: haloalkene with bromine on less sub. side
reactants: HBr and ROOR

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9
Q

Acid catalyzed hydration

A

reaction type: alkene
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: alcohol group on more sub. side of haloalkene
reactants: H2So4 and H2O

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10
Q

Halohydrin formation

A

reaction: alkene
intermediate: bridged triangle
regioselectivity: Markovnikov
stereoselectivity: anti selective
product: alcohol on more sub. side and halide
reactants: Br2 or CL2, H2O

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11
Q

Bromination of alkene

A

reaction type: alkene
intermediate: bridged intermediate
regioselectivity: Markovnikov
stereoselectivity: antiaddition
products: 2x bromine on either side of double bond
reactants: Br2 and CH2Cl2

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12
Q

Oxymercuration

A

reaction type: alkene
intermediate: bridged intermediate
regioselectivity: Markovnikov
stereoselectivity: none
products: addition of OH group
reactants: (Hg(OAc)2 and H2O)

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13
Q

Syn-hydroxylation of alkene

A

reaction type: alkene
intermediate: none
regioselectivity: Markovnikov
stereoselectivity: syn addition
products: glycol
reactants: OsO4 and H2O2

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14
Q

Hydroboration (BH3, THF) oxidation

A

reaction type: alkene
intermediate: none
regioselectivity: antimarkovnikov
stereoselectivity: syn addition
products: addition of OH group to less substituted side
reactants: BH3*THF, H2O2 and OH

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15
Q

Ozonlysis

A

reaction type: alkene
intermediate: none
regioselectivity: none
stereoselectivity: none
products: 2 aldehydes; cleavage of C=C
reactants: O3, (Ch3)2S

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16
Q

Catalyst of alkene

A

reaction type: alkene
intermediate: none
regioselectivity: none
stereoselectivity: none
products: alkene to alkane
reactants: H2 and catalyst

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17
Q

Free Radical Halogenation

A

reaction type: alkene
intermediate: radical
regioselectivity: antimarkovnikov
stereoselectivity: none
products: most stable double bond resonated form; Br on less sub. side
reactants: trace Br2 and light

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18
Q

Acid-Catalyzed Alcohol Addition

A

reaction type: alkene
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: methoxy group on more sub. side
reactants: CH3OH, H+

19
Q

Internal nucleophilic substitution in halohydrins

A

reaction type: alkene
intermediate: bridged intermediate
regioselectivity: Markovnikov
stereoselectivity: antiaddition
products: formation of an epoxide
reactants: X2 and H2O, NaH and H2O

20
Q

Oxidation of alkenes with Peroxycarboxylic acid

A

reaction type: alkene
intermediate: none
regioselectivity: none
stereoselectivity: syn addition
products: epoxide formation through concerted mechanism
reactants: MCPBA, CH2Cl2

21
Q

Acid/base

A

reaction type: alkyne
intermediate: carbanion
regioselectivity: Markovnikov
stereoselectivity: none
products: Na addition to 1 side of triple bond
reactants: NaNH2

22
Q

Extend the chain

A

reaction type: alkyne
intermediate: carbanion
regioselectivity: Markovnikov
stereoselectivity: none
products: internal alkyne
reactants: NaNH2, CH3X

23
Q

Acid Catalyzed hydration with Alkynes

A

reaction type: alkyne
intermediate: bridged intermediate
regioselectivity: Markovnikov
stereoselectivity: none
products: Ketone
reactants: HgSO4 and H2SO4, H2O

24
Q

Hydroboration (Sia2BH) Oxidation

A

reaction type: alkyne
intermediate: none
regioselectivity: antiarkovnikov
stereoselectivity: syn addition
products: aldehyde
reactants: Sia2 and BH, H2O2 and HO

25
Q

2nd Equivalent Bromination

A

reaction type: alkyne
intermediate: bridged intermediate
regioselectivity: Markovnikov
stereoselectivity: anti addition
products: 2 bromines on each side of double bond
reactants: Br2 and CCl4

26
Q

2nd equivalent of hydrogen halides

A

reaction type: alkyne
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: addition of 2x halides to same side
reactants: HX

27
Q

Lindlar catalyst

A

reaction type: alkyne
intermediate: N/A
regioselectivity: n/a
stereoselectivity: syn addition
products: cis alkene
reactants: H2 and lindlar

28
Q

Dissolving Metal reduction

A

reaction type: alkyne
intermediate: radical
regioselectivity: n/a
stereoselectivity: none
products: trans alkene
reactants: Na and NH3, CH3OH

29
Q

E1

A

intermediate: carbocation
base: weak (CH3)COH
solvent: pprotic
LG Preference: 3rd degree
markovnikov

30
Q

Pinacol Rearrangement

A

reaction: alcohol
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: ketone
reactants: H2SO4, heat (formed from glycol)

31
Q

Alcohol cleavage

A

reaction: alcohol
intermediate: none
regioselectivity: Markovnikov
stereoselectivity: none
products: ketone or aldehyde
reactants: HIO4

32
Q

H2CrO4, H2O and Acetone

A

forms carboxylic acid

33
Q

PCC, CH2Cl2

A

forms aldehyde

34
Q

Acid catalyzed bimolecular dehydration of alcohol

A

reaction: alcohol
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: ether product
reactants: H2SO4, temperature

35
Q

Silyl ethers as Protecting groups

A

chlorine is replaced by original structure

36
Q

Addition of Hydrogen Halides to alcohol

A

reaction: alcohol
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: Br on more substituted sire
reactants: HBr

37
Q

Addition of PBr3

A

reaction: alcohol
intermediate: none
regioselectivity: Markovnikov
stereoselectivity: anti addition
products: Br added to more sub. side on opposite face as LG
reactants: PBr3

38
Q

Additon of Cl via SOCl

A

reaction: alcohol
intermediate: none
regioselectivity: none
stereoselectivity: anti addition
products: Cl added to more sub side on opposite face as LG
reactants: SOCl, pyridine

39
Q

TSCl with Alcohol

A

reaction: alcohol
intermediate: none
regioselectivity: none
stereoselectivity: none
products: Hydrogen replaced by TS group
reactants: TSCl, Pyridine

40
Q

Acid catalyzed Elimination

A

reaction: alcohol
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: alkene
reactants: H2SO4, heat (formed from 1 OH)

41
Q

Williamson Ether Synthesis

A

reaction: alcohol
intermediate: none
regioselectivity: none
stereoselectivity: none
products: ether
reactants: NaH and Ch3X

42
Q

Acid Catalyzed Cleavage by HX

A

reaction: ether
intermediate: carbocation
regioselectivity: Markovnikov
stereoselectivity: none
products: Halide on either side of the cleaved ether
reactants: HBr (2eq), heat

43
Q

Acid Catalyzed ring opening

A

reaction: epoxide
intermediate: none
regioselectivity: Markovnikov
stereoselectivity: anti addition
products: alcohol and methoxy group
reactants: H2SO4 and CH3OH, heat
steps: protonate, attack, deprotonate

44
Q

Nucleophilic ring opening

A

reaction: epoxide
intermediate: none
regioselectivity: antiarkovnikov
stereoselectivity: antiaddition
products: alcohol and methoxy group
reactants: NaOCH3, CH3OH

Organic Chemistry 1 (2 decks)

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