O Chem Rxn Flashcards

0
Q

Halohydrin Formation

A
X2 over H2O.
Adds an X and an OH.
Halogen ion intermediate.
S: anti
R: Markovnikov, OH preferring higher substituted C
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1
Q

Addition of HX to Alkenes

A

Adds H and X.
S: N/A
R: Markovnikov

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2
Q

Acid Catalyzed Alkene Hydration

A

Adds H and OH.
Water removes proton, water is deprotonated, water joins molecule, water is deprotonated.

R: Mark, but not consistent since shifts are possible.

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3
Q

Oxymercuration of Alkenes

A

Adds H and OH.
S: anti
R: Markovnikov

  1. Hg(OAC)2, H2O/THF
  2. NaBH4

(Compare to hydroboration)

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4
Q

Hydroboration of Alkenes

A

Adds H and OH

S: Syn
R: non-Markovnikov
1. BH3/THF
2. H2O2, NaOH, H2O

(compare to oxymercuration)

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5
Q

Dichlorocarbene Addition

A

Forms cyclopropane with Halogens attached.
S:Syn
R: NA

CHCl3, KOH

(compare to Simmons-Smith)

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6
Q

Simmons-Smith

A

Forms cyclopropane without attached Halogens.

S: Syn
R: NA

CH2I2, Zn(Cu), ether

(compare to Dichlorocarbene addition)

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7
Q

Catalytic hydrogenation of Alkenes

A

Adds two H.

S: Syn
R: NA

H2, Pd/C or PtO2

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8
Q

Peroxyacid Epoxidation

A

Peroxyacid forms epoxide from Alkene. Acid adds 2 OH

S: anti
R: NA

  1. Peroxyacid
    2 H3O+

(acid step mimics X2 addition)
(compare result to OsO4 hydroxylation)

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9
Q

Hydroxylation with Osmium Tetraoxide

A

Adds 2 OH.

S: Syn
R: NA

  1. OsO4, pyridine
  2. NaHSO3, H2O

(compare to epoxide hydrolysis)

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10
Q

Oxidative Cleavage of Alkenes with Ozone

A

Splits DBs with DB Os.

  1. O3
  2. Zn, H3O+
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11
Q

Oxidative Cleavage of Alkenes with Potassium Permanganate

A

Splits DBs with DB Os.

R groups stay, 1 H becomes OH, 2 H becomes CO2.

KMnO4, H3O+

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12
Q

Bromohydrin Formation

A

Adds Br and OH.
Anti, Markovnikov.

NBS in H2O with DMSO.

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13
Q

Dehydrohalogenation of Vicinal Dihydrides

A

Forms alkyne from alkane.
2 KOH, ethanol
Or 2 NaNH2, NH3

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14
Q

Addition of HCl or HBr to alkynes

A

Markovnikov, usually trans. 2nd equivalent, Xs on same C.

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14
Q

Addition of Cl2 or Br2 to Alkynes

A

Anti. X2, CH2Cl2.

15
Q

Mercury Sulfite Catalyzed Hydration

A

Forms methyl ketone with enol intermediate.
Markovnikov
H2SO4, H2O, HgSO4

mechanism given.

16
Q

Hydroboration of Alkynes

A

Forms aldehyde. Non-Markovnikov.

  1. BH3 2. H2O2
17
Q

Catalytic Hydrogenation of Alkynes

A

2 H2, Pd/C gives complete reduction.

H2, Lindlar catalyst reduces to DB (cis)

18
Q

Lithium reduction

A

Reduces alkyne to DB (trans)
Li, NH3,

mechanism given

19
Q

Conversion of Alkynes to Acetylide anions

A

Forms TB with terminal anion.

NaNH2, NH3

20
Q

Alkylation of Acetylide Anions

A

Acetylene forms terminal alkyne.
Terminal alkyne forms internal alkyne.

  1. NaNH2 2. R’CH2Br

mechanism given.

21
Q

Oxidative cleavage of Alkynes

A

TB forms 2 DB Os.

Terminals become RCOOH (R group)
Or O=C=O (no R group)

22
Q

Alkyl Halides from Alcohols: HX

A

X replaces OH.
HX, ether.

Tertiary C is most reactive, then secondary, primary.

22
Q

Alkyl Halides from Alcohols: SOCl2

A

Cl replaces OH.
SOCl2, Pyridine.
Primary and secondary alcohols.

23
Q

Alkyl Halides from Alcohols: PBr3

A

Br replaces OH.
PBr3, ether.
Primary and secondary alcohols.

24
Q

Grignard Reagent Formation

A

RX + Mg, ether

Gives RMgX

25
Q

Gilman Reagent Formation

A
  1. RX + 2Li, pentane gives RLi and LiX
  2. RLi + CuI, ether gives RCuR- , Li+ and LiI.

Gilman reagents form hydrocarbons in organometallic coupling.

26
Q

Organometallic coupling

A

R2CuLi + R’X, ether gives RR’, and LiX

27
Q

Reduction of alkyl halides to alkanes

A

Grignard reagent RMgX in water gives RH and HOMgX.

28
Q

Reagent is nucleophile only: halides, sulfur, phosphorus.

A

1: sn2
2: sn2 & sn1
3: sn1

30
Q

Reagent is base only: H-, tBuO-, LDA.

A

E2

31
Q

Reagent is strong nucleophile & strong base:HO-, MeO-, EtO-.

A

1: sn2 major, e2 minor.
2: e2 major, sn2 minor.
3: e2.

32
Q

Reagent is weak base & weak nucleophile: H2O, MeOH, EtOH.

A

1: sn2 or e2, too slow to use.
2: anybody. Alcohols do e1 with H2SO4 and heat.
3: hot e1, cool sn1.

33
Q

Allylic Bromination

A

Adds Br to C adjacent a DB.

NBS, CCl4, hv

34
Q

Add chain to OH

A

NaH, RX

35
Q

Diels-Alder

A

Conjugated Alkene grabs dienophile (DB one bond from C=O or C TB N) to form 6 membered ring with one DB (opposite dienophile).

Endo product: syn to larger ring.