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Organic Chemistry > Exam 3 > Flashcards

Exam 3 Flashcards

1
Q

Alkyne Start

Reduction:

(Two Equivalents) -H2

-Pt, Pd, or Ni

A

Catalytic Hydrogenation (trans)

Added: -H (x4)

  • Regiochem: None
  • Stereochem: Syn-addition
  • Formed: Cis-intermediate, but it’s too unstable so contiues into Trans Alkane
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2
Q

Alkyne Start

Reduction:

(one equivalent) -H2

-Lindler’s Catalyst or Ni2B

A

Catalytic Hydrogenation (cis)

  • Added: -H -H
  • Regiochem: No
  • Stereochem: Syn-addition
  • Forms: Cis Alkene
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3
Q

Alkyne Start

Reduction:

  • Na
  • NH3(liquid)
A

Dissolving Metal Reduction

  • Added: -H -H
  • Regiochem: No
  • Stereochem: Anti-addition
  • Forms: Trans Alkene
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4
Q
  • Alkyl Dihalide (geminal or vicinal)
    1) Excess NaNH2/NH3
    2) H2O
A

Formation of Alkynes

Added: Two Pi bonds

Regiochem: N/A

Stereochem: N/A

-Formed: Alkyne (resulting alkyne must be less acidic than reagent acid)

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5
Q

Alkyne Start

Addition:

(One Equivalent) -HX

A

Hydrohalogenation

  • Added: -H -X
  • Regiochem: Markovnikov
  • Stereochem: N/A
  • Formed: Alkene
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6
Q

Alkyne Start

Addition:

-Excess HX

A

Hydrohalogenation

  • Added: -H -H -X -X
  • Regiochem: Markovnikov
  • Stereochem: N/A
  • Formed: Alkane (Geminal dihalide)
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7
Q

Alkyne Start

Addition:

-HBr, ROOR

A

Radical Addition of Br

  • Added: -H -Br
  • Regiochem: Anti-Markovnikov
  • Stereochem: N/A
  • Formed: MIxture of E&Z Alkenes

*Only works on terminal alkynes

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8
Q

Alkyne Start

Addition:

  • H2SO4/H2O or H3O+
  • HgSO4
A

Acid Catalyzed Hydration

  • Added: -H -OH
  • Regiochem: Markovnikov
  • Stereochem: N/A
  • Formed: Ketone (major) with an Enol intermediate

*When asked for product, only show ketone. Show formation of Enol when asked for mechanism!

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9
Q

Alkyne Start

Addition:

1) Disiamylborane or 9-BBN2
2) NaOH/H2O2

A

Hydroboration/Oxidation

  • Added: -H -OH
  • Regiochem: Anti-markovnikov
  • Stereochem: N/A
  • Formed: Aldehyde is major product with Enol intermediate

*when asked for products only draw Aldehyde. When asked for mechanism, draw formation of Enol!

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10
Q

Alkyne Start

Addition:

  • Excess Cl2 or Br2
  • CCl4
A

Halogenation (in excess)

  • Added: -Cl or Br (x4)
  • Regiocem: N/A
  • Stereochem: N/A
  • Formed: Tetrahaloalkane (alkane with FOUR halogen groups)
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11
Q

Alkyne Start

Addition:

  • (One equivalent) Cl2 or Br2
  • CCl4
A

Halogenationof One Equivalent

  • Added: -Cl or Br -Cl or Br
  • Regiochem: N/A
  • Stereochem: Anti-addition-

Formed: Alkene with TWO halogen groups

_*E is MAJOR and Z is minor_

E is opposite sides, Z is same!

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12
Q

Addition of an internal Alkyne:

1) O3
2) H2O

A

Ozonolysis of Internal Alkyne-

Added: Triple bond cleaved, -O added to end of double bond and -OH added to other side

  • Regiochem: N/A
  • Stereochem: N/A
  • Formed: TWO Carboxylic acids
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13
Q

Alkene Start

Addition:

-HX

A

Hydrohalogenation (Markov)

  • Added: -H -X
  • Regiochem: Markovnikov
  • Stereochem: Racemic Mix
  • Rearrange: YES (carbocation formed/mix of rearranged and not rearranged)
  • Forms: Alkane (halide)
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14
Q

Alkene Start

Addition:

  • HBr
  • ROOR
A

Hydrohalogenation

  • Added: -H -Br-
  • Regiochem: Anti-Makovnikov
  • Stereochem: N/A?
  • Rearrange: NO, no carbocation
  • Forms: Alkane
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15
Q

Alkene Start

Addition:

-H3O+ or H2O, [H2SO4]

A

Acid Catalized Hydration

  • Added: -H -OH
  • Regiochem: Markovnikov
  • Stereochem: Racemic mix
  • Rearrange: YES (carbocation formed)

_*results in mixture of rearranged and not_

-Forms: Alkane

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16
Q

Alkene Start

Addition:

1) Hg(OAc)2/H2O
2) NaBH4

A

Oxymercuration

  • Added: -H -OH
  • Regiochem: Markovnikov
  • Stereochem: Anti-addition?
  • Rearrange: NO, no carbocation (forms mercurinium ion)
  • Forms: Alkane

*any nucleophile can be used instead of H2O, but water is the main one used

17
Q

Alkene Start

Addition:

1) BH3•THF
2) NaOH/H2O2

A

Hydroboration/Oxidation

  • Added: -H -OH
  • Regiochem: Anti-markovnikov
  • Stereochem: Syn-addition
  • Rearrange: NO, concerted
  • Forms: Alkane
18
Q

Alkene Start

Addition:

  • H2
  • Pt, Pd, or Ni
A

Catalytic Hydrogenation

  • Added: -H -H
  • Regiochem: N/A
  • Stereochem: Syn-addition
  • Rearrange: NO, no carbocation (concerted)
  • Forms: Alkane

*One chirality center formed= syn-addition not relevant/one product formed, two chirality= both enantiomers formed, three chirality= requirement for syn determines what enantiomers are formed

19
Q

Alkene Start

Addition:

-X2 (Cl or Br only)

A

Halogenation

  • Added: -X -X
  • Regiochem: N/A
  • Stereochem: Anti-addition
  • Rearrange: NO, no carbocation (bromium or chloronium ion formed, not concerted)
  • Formed: Dihalide alkane (geminal)

*If starting alkene is Cis= two products formed (enantiomer), Trans alkene= one product (meso)

20
Q

Alkene Start

Addition:

  • X2 (Br or Cl only)
  • H2O
A

Halodrin Formation

  • Added: -X -OH
  • Regiochem: X= Anti-markovnikov, OH= Markovnikov
  • Stereochem: Anti-addition (enantiomer is formed)
  • Rearrange: NO, bromium or chlorium ion formed
  • Formed: Alkane with an alcohol and halogen group
21
Q

Alkene Start

Addition:

1) RCO3H or MCPBA
- H3O+

A

Anti-Dihydroxylation

  • Added: -OH -OH
  • Regiochem: N/A
  • Stereochem: Anti-addition
  • Rearrange: NO, no carbocation. EPOXIDE FORMS
  • Formed: Trans Diols (Enantiomer forms)
22
Q

Alkene Start

Addition:

1) OsO4
2) NaHSO3/H2O

A

Syn-Dihydroxylation

  • Added: -OH -OH
  • Regiochem: N/A
  • Stereochem: Syn-addition
  • Rearrange: NO, no carbocation OR EPOXIDE
  • Forms: Cis Diols (meso)
23
Q

Alkene Start

Addition:

1) O3
2) DMS

A

Ozonolysis

  • Added: Double bond cleaved and -O added to ends of double bonds, -H to the side that needs it
  • Regiochem: N/A
  • Stereochem: N/A
  • Rearrange: YES, but no carbocation. Initial Ozonide will rearrange to form more stable one
  • Formed: If not symetrical, draw both halves that are formed. If symetrical, you can draw both but indicate that they are the same
24
Q

Alkane to Alkene

A

Alkane must have good leaving group, and the correct sized strong base is used. Formed via Elimination

25
Q

Alkene to Alkyne

A

1) Br2, CCl4 (forms a geminal alkane)
2) Excess NaNH2 (last two steps add two Pi bonds)
3) H2O

26
Q

Alkyne to Cis-Alkene

A

-H2, Lindler’s Catalyst

(cis doesn’t matter if terminal alkyne)

27
Q

Alkyne to Trans-Alkene

A

-Na, NH3 (liquid)

(trans doesn’t matter if terminal alkyne)

28
Q

Alkene to Alkane without adding substituents

A
  • H2
  • Pt, Pd, or Ni
29
Q

Alkene to Alkane with adding substituents

A

Any of the Alkene addition reactions

30
Q

Alkyne to Alkane (vicinal dihalide)

A

-Excess HX

31
Q

Alkyne to Alkane without adding substituents

A

-Two equivalents H2/Pt, Pg, or Ni

Organic Chemistry (2 decks)

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