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Z - Chem 2210 (S&T) > Chapter 8 > Flashcards

Chapter 8 Flashcards

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1
Q

What happens during an Alkene Addition of H-X? Do we need to know the mechanism?

A

Hydrogen attaches to the least substituted C of the double bond, producing a carbocation. After a potential carbocation rearrangement, the halogen attaches to the carbocation

X attaches the the most substituted side, with possible carbocation rearrangement

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2
Q

What are the substrates in an Oxymercuration/Demurcuration reaction?

A

Hg(OAc)2/THF/H20

NaBH4/OH-

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3
Q

What happens in a oxymercuration/demercuration reaction? Do we need to know the mechanism?

A

Use Hg(OAc)2/THF/H20, then NaBH4/OH-

OH goes to the most substituted side, the H goes to the least substituted side (always)

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4
Q

What are the substrates for an Acid Catalyzed Hydrogenation?

A

Acid(ex: H+, dilute)/H2O

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5
Q

What happens in an Acid Catalyzed Hydrogenation? Do we need to know the mechanism?

A

The OH goes to the most substituted side, the H goes the least substituted side. There is a possible carbocation rearrangement, so we need to know the mechanism.

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6
Q

What are the substrates for a Hydroboration/Oxidation Reaction?

A

BH3/THF

H2O2/NaOH

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7
Q

What happens in a Hydroboration/Oxidation Reaction? Do we need to know the mechanism?

A

Use BH3/THF then H2O2/NaOH

The OH goes to the least substituted side, the H goes to the most substituted side (always)

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8
Q

What happens in an Addition reaction of Dihalogens (X2) in Organic Solvents? Do we need to know the mechanism?

A

The Halogen(X) is added to each carbon of the double bond (diagonal from each other) We do not need to know the mechanism.

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9
Q

What happens in an Addition reaction of Dihalogens(X2) in Water? Do we need to know the mechanism?

A

A Halogen(X) is added to the least substituted side, the OH goes to the most substituted side

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10
Q

What happens in an Oxidation reaction of Alkenes with COLD/DILUTE Permanganate in basic solution? Do we need to know the mechanism?

A

An OH is added to each carbon of the double bond syn. (forming Cis-1,2-diols) We do not need to know the mechanism.

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11
Q

What happens in an Oxidation reaction of Alkenes with Osmium Tetroxide (OsO4)? Do we need to know the mechanism?

A

An OH is added to each carbon of the double bond syn. (forming Cis-1,2-diols) We do not need to know the mechanism.

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12
Q

What happens in an Oxidative Cleavage reaction of Alkenes with HOT, basic Permanganate, then H+? Do we need to know the mechanism?

A

Depending on the alkene, different products will form. A double bond O will replace the double bond on each side, and an OH will replace each H bonded to the carbons.

H2C= -> (OH)2C=O (Carbonic Acid) -> CO2 +H2O

RHC-> (OH)(R)C=O (Carboxylic Acid)

R2C -> R2C=O (Ketone)
We do not need to know the mechanism

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13
Q

What happens in a Cleavage of Alkenes via Ozonolysis (O3) reaction (Me2S is also added)? Do we need to know the mechanism?

A

Depending on the alkene, different products will form. The double bond will be cleaved by oxygen; oxygen will attach to the double bond on both sides. This will form either aldehydes (at least one H) or ketones.
We do not need to know the mechanism.

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14
Q

What happens in an Addition Reaction to Alkynes? Do we need to know the mechanism?

A

Each time you add HX, the H will go to the less substituted side and the X will attach to the more substituted side. If you do the reaction twice, the two halogens will attach to the same side/carbon (forming a geminal dihalide). We do not need to know the mechanism.

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15
Q

What happens in an Addition reaction of Dihalogens(X2) to Alkynes in Organic solvents? Do we need to know the mechanism?

A

The Halogens will attach on opposite sides (diagonal), first forming an alkene with a halogen on each side, then an alkane with two halogens on each side. We do not need to know the mechanism.

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16
Q

What are the possible substrates in a Hydrogenation of Alkyne reaction? What products will they produce?

A

NiB2(P-2) or Pd/CaCO3 produces Cis-Alkenes,

Li/NH3 or Na/NH3 produces Trans-Alkenes,

Pd/Ni/Pt/Rh/Ru produces an Alkane

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17
Q

Alkene + HX -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkyl Halide, halogen on most substituted side of double bond.

Possible carbocation rearrangement. Produces Enantiomers because trigonal planar. (racemic mixture).

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18
Q

Alkene + H+/H2O -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alcohol, OH on the most substituted side of double bond.

Possible carbocation rearrangement. Produces Enantiomers because trigonal planar. (racemic mixture)

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19
Q

Alkene + Hg(OAc)2/THF/H2O + NaBH4/OH- -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alcohol, OH goes to the most substituted side of double bond. No possible carbocation rearrangement or enantiomers. Anti addition.

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20
Q

Alkene + BH3/THF + H2O2/NaOH -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alcohol + NaBO3 + H2O, OH goes to the LEAST substituted side,

No carbocation, syn addition, enantiomers are produced.

21
Q

Alkene + X2 in CCl4 (organic solvent) -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkane with Anti-Addition of Halogens. Produces Enantiomers if Cis-Alkene. (cis=enantiomers, trans=meso, but check for symmetry)

22
Q

Alkene + X2 in H2O -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkane Halohydrin, X and OH are added across the double bond in an anti addition. No carbocation. OH goes to the most substituted side. Enantiomers are produced.

23
Q

Alkene + COLD/DILUTE Permanganate -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Cis-1,2-diols, OH is added to both of the carbons of the double bonds, syn. May produce enantiomers, depending on starting alkene.

24
Q

Alkene + Osmium Tetroxide -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Cis-1,2-diols, OH is added to both of the carbons of the double bonds, syn. May produce enantiomers, depending on starting alkene.

25
Q

Alkene + HOT Permanganate/OH -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Carboxylic Acid, Ketone, or CO2/H2O, each side of the double bond is cleaved by Oxygen, and every Hydrogen is replaced with an OH Group.

26
Q

Alkene + O3 -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Different products are produced, a double bond is cleaved by Oxygen (R=R -> R=O + R=O)

27
Q

Alkyne + 1HX -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkene with the halogen on the most substituted side, with H added anti.

No enantiomers due to double bond

28
Q

Alkyne + 2HX -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Geminal Dihalide, both halogens attached to same carbon, on the most substituted side

29
Q

Alkyne + 1X2 in CCl -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkene with halogens on opposite sides (anti addition)

No enantiomers due to double bond

30
Q

Alkyne + 2X2 in CCl -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkane with 4 halogens where triple bond was

31
Q

Alkyne + H2 with NiB2(P-2) or Pd/CaCO -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Cis-Alkene

32
Q

Alkyne + Li/NH3 or Na/NH3 -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Trans-Alkene

33
Q

Alkyne + H2 with Pd/Ni/Pt/Rh/R -> ?

Carbocation rearrangement? Stereochemistry? Syn, anti, or N/A?

A

Alkane

34
Q

How do you produce an Alkyl Halide from an Alkene?

A

Add a HX

35
Q

How do you produce an Alcohol (OH on most substituted side) from an Alkene? (one step, possible rearrangement)

A

Add a dilute acid in water (has to be enough water to react)

36
Q

How do you produce an Alcohol (OH on most substituted side) from an Alkene? (Two step, no rearrangement)

A

Add Hg(OAc)2/THF/H2O (Oxymercuration) and NaBH4/OH- (Demurcuration)

37
Q

How do you produce an Alcohol (OH on least substituted side) from an Alkene? (Two step method, no rearrangement)

A

Add BH3/THF (Hydroboration) and H2O2/NaOH (Oxidation)

38
Q

How do you produce an Alkane with Anti-Addition of (2)Halogen from an Alkene?

A

Add X2 in an organic solvent (CCl4)

39
Q

How do you produce an Alkane Halohydrin from an Alkene? (Halogen and OH group anti addition)

A

Add X2 + H2O

40
Q

How do you produce a Cis-1,2-diol (OH attached to each carbon from the double bond) from an Alkene?

Two possible methods

A

Two methods: Add Cold/DIlute Permanganate(KMnO4) OR Add Osmium Tetroxide (OsO4)

41
Q

How do you add Oxygen to the Hydrogens of an Alkene, and split the double bond with oxygen?

A

Add Hot Permanganate (KMnO4) and OH-, this produces ketones, carboxylic acid, or carbonic acid (which degrades to CO2 and H2O_

42
Q

How do you Cleave Alkenes with Oxygen?

A

Add O3

43
Q

How do you produce an Alkene with a Hydrogen and a Halogen attached from an Alkyne?

A

You add HX to the Alkyne. The H will go to the least substituted side, the X to the most

44
Q

How do you produce a Geminal Dihalide (An Alkane with two halogens on most substituted side, two carbons on the other) from an Alkyne?

A

You add 2HX to the Alkyne. The H will go to the least substituted side, the X to the most

45
Q

How do you produce a Cis-Alkene from an Alkyne? (no substituents)

A

Add H2 with NiB2(P-2) or Pd/CaCO3

46
Q

How do you produce a Trans-Alkene from an Alkyne? (no substituents)

A

Add Li/NH3 or Na/NH3

47
Q

How do you produce an Alkane from an Alkyne? (no substituents)

A

Add Pd/Ni/Pt/Rh/Ru

48
Q

What is the structure of MsCl?

A

CH3SO2Cl

49
Q

What is the structure of TsCl?

A

toluene-SOOCl

Z - Chem 2210 (S&T) (14 decks)

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