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O Chem Mech 2 > Mechanisms And Facts > Flashcards

Mechanisms And Facts Flashcards

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1
Q

What does attack of the alkenes refer to?

A

Like EAS, alkenes attack E+ but need less motivation so no super E+ is needed, and addition occurs where a pi bond becomes 2 new sigma bonds. Reverse of elimination!

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2
Q

How to add a sigma bonded halogen?

A

Halo-hydrin (HBr), (syn/anti) Mar (C+)

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3
Q

What is Markovnikov’s rule

A

Put + or carbocation on most stable position, first sigma (H) on less substituted carbon

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4
Q

How to add an alcohol sigma bond

A

Hydration (H2O, cat. acid), Syn/anti Mar (C+)

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5
Q

What is Markovs addition?

A

Add -OH on most substituted

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6
Q

Syn addition

A

Nu only attacks same side as first group (maybe bc mechanism)

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7
Q

Anti addition

A

Nu only attacks opposite side from 1st group, (something in way on other side?)

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8
Q

How to add an alcohol with r group

A

Basically hydration (R-OH, cat. acid), Syn/anti, Mar (C+)

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9
Q

How to add two halogens

A

Halogenation (X2), Markov addition, Anti; polarizability is why no catalyst is needed

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10
Q

How to add a halogen and alcohol

A

Halo-hydration (X2, H2O), Anti, Mar; similar halogenation but done in weak Nu solvent, X is better Nu but there is so much water that H2O is added

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11
Q

How to add OH without rearrangement

A

Mercuration* (1)Hg(OAc)2, H2O 2)NaBH4), Anti, Markov addition with no rearrangement

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12
Q

How to add OH group to less substituted position (not base)

A

*(1)BH3 2) HOOH/OH-), syn, non markov add bc mechanism and sterics

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13
Q

How to make an alkene into an alkane

A

Hydrogenation* (H2 gas, Cat. Pd/C), syn

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14
Q
A
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15
Q

How to control the second addition at will

A

Epoxides (mCPBA)

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16
Q

How to make epoxide which inverts steriochem 2 x

A

(1)Br2 in H2O 2) LDA), anti

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17
Q
Difference in additions
A
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18
Q

How to attack less hindered in epoxide

A

Base no carbocation so attacks less hindered spot

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19
Q

How to attack most stable in epoxide

A

Acid bc carbocation is formed

20
Q

How to break c-c bond

A

Cleaver*, ozonolysis

21
Q

How to make ozone

A

Ozonolysis, ozone breaks down molecules bc its super reactive, DMSO is stable, Malozonide (3 O right next to each other) intermediate is super unstable

22
Q

Difference in external and internal alkynes

A

External has a relatively acidic proton which is removed by strong bases. Both have 2 pi bonds to react

23
Q

How to make alkynes

A

Internal Br2 2 eq LDA
External Br2 3 eq LDA and H2O

24
Q

How to make geminal dibromide

A
25
Q

How to add 4 Br

A

Halogenation with alkenes (Br2)

26
Q

How to make a ketone

A

Alkyne hydration (H2O, Cat. H2SO4), enol tautomerizes keto aldehyde, water best nu and base

27
Q

Mercuration with alkyne

A

Cant do that

28
Q

Non markov add for aldehyde

A

(1)BH3 2) NaOH, HOOH) Makes aldehyde

29
Q

How to add H2 to alkyne

A

Hydrogenation, H2 with pd/c, lindlars, then Na and NH3

30
Q

How to break an alkyne

A

Cleaver (1) O3 2) SMe2, 3 bonds O each

31
Q

Practice oxidation here, what is it?

A

Look for H on home C, add more bonds to O (from H)

32
Q

Strong oxidizing agent on secondary

A

Jones (H2CrO4, H2O)

33
Q

Strong oxidizing agent with primary

A

Jones, needs OH group as enabler, water is best Nu

34
Q

Oxidize primary alcohol once

A

No water bc if there is any it makes a geminal diol (no second oxidation without water), PCC can only make ketones or aldehydes

35
Q

Reminders

A
36
Q

Add OH with multiple groups present

A

Tollens reagent, (Ag2(OH), NH4OH), reacts with double bonded O’s C

37
Q

Carbon connected to benzene reactivity

A

Benzylic resonance stabilized leads to more reactivity

38
Q

Add carboxylic acid to ring

A

Jones, good to bad group, changing activation group

39
Q

Complete the rxns

A
40
Q

Solve

A
41
Q

Add halogen next to carbonyl

A

Tetrahedral intermediate (SOCl2, cat. Py)

42
Q

Solve

A

No… OH, never use OH with LDA bc takes proton

43
Q

Solve

A
44
Q

How to form an ester, what happens if base present

A
45
Q

3 ways make this

A
46
Q

How many solutions

A

Usually 4 but 2 same, syn or ant make 2

O Chem Mech 2 (1 decks)

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