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Addition Reactions Flashcards

1
Q

What is needed for hydrohalogenation? What are the steps? What kind of addition?

A
  • HX
  • Pi bond attacks H and Halide attacks +
  • Markovnikov
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2
Q

What reagent is needed for hydrohalogenation to be antimarkovnikov addition?

A

ROOR

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3
Q

What are the steps of hydrohalogenation with ROOR?

A
  • ROOR breaks into 2 OH radicals
  • Radicals propogate HX into H2O and X radical
  • X radical attacks more substituted side
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4
Q

What is needed for hydration? What are the steps? What kind of addition?

A
  • dilute H2SO4
  • Proton transfer, carbocat rearrangement, water attacks +, water attacks intermediate to make H3O+
  • markovnikov
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5
Q

What reagent is needed to make hydration an antimarkovnikov addition reaction?

A

BH3*THF/H2O2, NaOH

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6
Q

What is needed for catalytic hydrogenation? What are the steps? What kind of addition?

A
  • H2/PT
  • Metal surface holds down substrate and pi bond breaks
  • syn addition
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7
Q

What is needed for halogenation? What kind of addition?

A
  • BR2/CCl4
  • antiaddition
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8
Q

What is needed for halohydrin formation? What are the steps? What kind of addition?

A
  • X2/H2O
  • OH adds to more substituted carbon and X adds to the other
  • Antiaddition
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9
Q

What is needed for anti-dihydroxylation? What kind of addition?

A

1.mCPBA/2. H3O+
Antiaddition

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10
Q

What are the steps of anti-dihydroxylation?

A
  1. H attacks C
  2. Pi bond attacks O
  3. Bond between Os attacks bond over
  4. Epoxide initiates proton transfer
  5. Water attacks carbon to attack + on O
  6. Watr attacks again to make H3O+ and diols
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11
Q

What is important to check for with anti-dihydroxylation? How do you check?

A

Meso compounds
Look for opposite configurations

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12
Q

What reagent is needed for oxidative cleavage? What happens in the products?

A

O3/DMS
All pi bonds break into aldehydes/carbonyls

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13
Q

What is needed for syn-dihydroxylation? What kind of addition?

A

OsO4 (catalytic)/NMO — synaddition
KMnO4, NaOH/cold — antiaddition

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14
Q

What is needed for alkyne formation? What are the steps?

A

1.xs NaNH2/2. H2O

  1. NH2 attacks beta H
  2. Double bond forms
  3. LG leaves
  4. Repeats to form alkyne
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15
Q

What is needed for alkylating terminal alkenes? What is the process?

A
  1. NaNH2 (can be xs)/ 2. Alkyl Halide
  2. NH2 attacks H
  3. lone pair attacks alpha carbon
  4. LG leaves
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16
Q

What is needed for alkyne reduction? What are the products?

A

H2/Lindlars — cis alkene
Na/NH3 (L) — trans alkene
H2/Pt. — alkane

17
Q

What are the steps of alkyne reduction with Na/NH3?

A
  1. Na radical attacks triple bond
  2. single radical and double radical form on opposite sides of triple bond
  3. double radical attacks H on NH3 and bond breaks
  4. Na radical attacks single radical
  5. double radical attacks NH3
18
Q

What is needed for the markovnikov addition version of hydrohalogenation of alkynes?

A
  1. xs NaNH2/NH3 / 2. H2O 3. HBr
19
Q

What is needed for the antimarkovnikov version of hydrohalogenation of alkynes?

A
  1. xs NaNH2/NH3 / 2. H2O 3. HBr, ROOR
20
Q

What is needed for the hydration of alkynes?

A

H2SO4, H2O/ HgSO4 — carbonyl will be on more substituted end

  1. 9-BBN/2. H2O2, NaOH — carbonyl will be on less substituted end
21
Q

What are the steps of enol-keto tautomerization in the presence of an acid?

A
  1. Proton transfer
  2. Resonance
  3. Proton transfer
22
Q

What are the steps of enol-keto tautomerization in the presence of an acid?

A
  1. Proton transfer
  2. resonance
  3. proton transfer

Orgo - Reaction Mechanisms (3 decks)

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