orgo I rxns

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ch 6-9

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22 Terms

1

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<p>reagents: H-Nu (addition of H2O, HX, or ROH)</p>

reagents: H-Nu (addition of H2O, HX, or ROH)

mechanistic notes: conjugate addition often thermodynamic product, direct addition is kinetic product
notes: 1,4-addition (conjugate), competes w/ 1,2-addition (direct)

<ul><li><p>mechanistic notes: conjugate addition often thermodynamic product, direct addition is kinetic product</p></li><li><p>notes: 1,4-addition (conjugate), competes w/ 1,2-addition (direct)</p></li></ul><p></p>

2

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<p>reagent: dienophile</p>

reagent: dienophile

mechanistic notes: regiochemistry determined by EWG & EDG, always forms 6 membered ring
notes: diels-alder rxn, ____

<ul><li><p>mechanistic notes: regiochemistry determined by EWG & EDG, always forms 6 membered ring</p></li><li><p>notes: diels-alder rxn, ____</p></li></ul><p></p>

3

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<p>reagent: neutral nucleophile (ends w Nu)</p>

reagent: neutral nucleophile (ends w Nu)

mechanistic notes: racemic product, solvents like H2O, ROH, RNH2 (neutral amines) as nucleophile
notes: SN1, occurs w/ E1, favored at lower temps

<ul><li><p>mechanistic notes: racemic product, solvents like H2O, ROH, RNH2 (neutral amines) as nucleophile</p></li><li><p>notes: SN1, occurs w/ E1, favored at lower temps</p></li></ul><p></p>

4

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<p>reagent: neutral nucleophile (ends w double bond)</p>

reagent: neutral nucleophile (ends w double bond)

mechanistic notes: always zaitsev product, requires beta H, solvents like H2O, ROH, RNH2 (neutral amines) as nucleophile
notes: E1, occurs w/ SN1, favored at higher temps

<ul><li><p>mechanistic notes: always zaitsev product, requires beta H, solvents like H2O, ROH, RNH2 (neutral amines) as nucleophile</p></li><li><p>notes: E1, occurs w/ SN1, favored at higher temps</p></li></ul><p></p>

5

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<p>reagent: strong nucleophile (charged)</p>

reagent: strong nucleophile (charged)

mechanistic notes: inversion of stereochemistry, always favored for primary alkyl halides, favored for secondary if weak base (NaCN, NaSH)
notes: SN2, may occur w/ E2

<ul><li><p>mechanistic notes: inversion of stereochemistry, always favored for primary alkyl halides, favored for secondary if weak base (NaCN, NaSH)</p></li><li><p>notes: SN2, may occur w/ E2</p></li></ul><p></p>

6

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<p>reagent: strong base (charged)</p>

reagent: strong base (charged)

mechanistic notes: hofmann if large strong base (tBuOH), zaitsev if small strong base, always favored for tertiary alkyl halides, favored for secondary if strong base
notes: E2, can occur w/ SN2, favored at higher temps

<ul><li><p>mechanistic notes: hofmann if large strong base (tBuOH), zaitsev if small strong base, always favored for tertiary alkyl halides, favored for secondary if strong base</p></li><li><p>notes: E2, can occur w/ SN2, favored at higher temps</p></li></ul><p></p>

7

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<p>reagents: HCl, HBr, HI (1 eq)</p>

reagents: HCl, HBr, HI (1 eq)

regiochemistry? markovnikov (X to more substituted carbon)
stereochemistry? none
notes: excess reagent forms geminal dihalide

<ul><li><p>regiochemistry? markovnikov (X to more substituted carbon)</p></li><li><p>stereochemistry? none</p></li><li><p>notes: excess reagent forms geminal dihalide</p></li></ul><p></p>

8

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<ul><li><p>reagents: Cl2, Br2 (organic solvent) (1 eq)</p></li></ul><p></p>

reagents: Cl2, Br2 (organic solvent) (1 eq)

regiochemistry? N/A
stereochemistry? anti-addition, trans halogenation
notes: excess reagent forms tetrahalide

<ul><li><p>regiochemistry? N/A</p></li><li><p>stereochemistry? anti-addition, trans halogenation</p></li><li><p>notes: excess reagent forms tetrahalide</p></li></ul><p></p>

9

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<p>reagents: H2O, H2SO4</p>

reagents: H2O, H2SO4

regiochemistry? markovnikov (OH to more substituted carbon)
stereochemistry? N/A, pdt immediately tautomerizes
notes: makes ketone final pdt, terminal alkenes need HgSO4 catalyst

<ul><li><p>regiochemistry? markovnikov (OH to more substituted carbon)</p></li><li><p>stereochemistry? N/A, pdt immediately tautomerizes</p></li><li><p>notes: makes ketone final pdt, terminal alkenes need HgSO4 catalyst</p></li></ul><p></p>

10

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<p>reagents: 1. 9-BBN, THF</p><ol start="2"><li><p>-OH, H2O2, H2O</p></li></ol><p></p>

reagents: 1. 9-BBN, THF

-OH, H2O2, H2O

regiochemistry? anti-markovnikov (OH to less substituted carbon)
stereochemistry? N/A, pdt immediately tautomerizes
notes: makes ketone or aldehyde final pdt

<ul><li><p>regiochemistry? anti-markovnikov (OH to less substituted carbon)</p></li><li><p>stereochemistry? N/A, pdt immediately tautomerizes</p></li><li><p>notes: makes ketone or aldehyde final pdt</p></li></ul><p></p>

11

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<p>reagents: H2, Pd/C</p>

reagents: H2, Pd/C

regiochemistry? N/A
stereochemistry? none

<ul><li><p>regiochemistry? N/A</p></li><li><p>stereochemistry? none</p></li></ul><p></p>

12

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<p>reagents: H2, Lindlar’s catalyst</p>

reagents: H2, Lindlar’s catalyst

regiochemistry? N/A
stereochemistry? cis hydrogenation

<ul><li><p>regiochemistry? N/A</p></li><li><p>stereochemistry? cis hydrogenation</p></li></ul><p></p>

13

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<p>reagents: Na or Li, NH3</p>

reagents: Na or Li, NH3

regiochemistry? N/A
stereochemistry? trans hydrogenation

<ul><li><p>regiochemistry? N/A</p></li><li><p>stereochemistry? trans hydrogenation</p></li></ul><p></p>

14

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<p>reagents: HCl, HBr, HI</p>

reagents: HCl, HBr, HI

regiochemistry? markovnikov (Cl to more substituted carbon)
stereochemistry? none
carbocation rearrangements? yes

<ul><li><p>regiochemistry? markovnikov (Cl to more substituted carbon)</p></li><li><p>stereochemistry? none</p></li><li><p>carbocation rearrangements? yes</p></li></ul><p></p>

15

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<p>reagents: H2O, H2SO4</p>

reagents: H2O, H2SO4

regiochemistry? markovnikov (OH to more substituted carbon)
stereochemistry? none
carbocation rearrangements? yes

<ul><li><p>regiochemistry? markovnikov (OH to more substituted carbon)</p></li><li><p>stereochemistry? none</p></li><li><p>carbocation rearrangements? yes</p></li></ul><p></p>

16

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<p>reagents: ROH, H2SO4</p>

reagents: ROH, H2SO4

regiochemistry? markovnikov (OR to more substituted carbon)
stereochemistry? none
carbocation rearrangements? yes

<ul><li><p>regiochemistry? markovnikov (OR to more substituted carbon)</p></li><li><p>stereochemistry? none</p></li><li><p>carbocation rearrangements? yes</p></li></ul><p></p>

17

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<p>reagents: 1. BH3, THF</p><ol start="2"><li><p>-OH, H2O2, H2O</p></li></ol><p></p>

reagents: 1. BH3, THF

-OH, H2O2, H2O

regiochemistry? anti-markovnikov (OH to less substituted carbon)
stereochemistry? syn-addition
carbocation rearrangements? no

<ul><li><p>regiochemistry? anti-markovnikov (OH to less substituted carbon)</p></li><li><p>stereochemistry? syn-addition</p></li><li><p>carbocation rearrangements? no</p></li></ul><p></p>

18

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<p>reagents: Cl2, Br2 (organic solvent)</p>

reagents: Cl2, Br2 (organic solvent)

regiochemistry? none
stereochemistry? anti-addition
carbocation rearrangements? no

<ul><li><p>regiochemistry? none</p></li><li><p>stereochemistry? anti-addition</p></li><li><p>carbocation rearrangements? no</p></li></ul><p></p>

19

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<p>reagents: Cl2, Br2 (water or alcohol as solvent)</p>

reagents: Cl2, Br2 (water or alcohol as solvent)

regiochemistry?
stereochemistry?
carbocation rearrangements? no

<ul><li><p>regiochemistry?</p></li><li><p>stereochemistry?</p></li><li><p>carbocation rearrangements? no</p></li></ul><p></p>

20

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<p>reagents: </p>

reagents:

regiochemistry?
stereochemistry?
carbocation rearrangements? no

21

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<p>reagents: </p>

reagents:

regiochemistry?
stereochemistry?
carbocation rearrangements? no

22

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<p>reagents: </p>

reagents:

regiochemistry?
stereochemistry?
carbocation rearrangements? no