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Organic Chemistry 2 > Reactions for Quiz 1 > Flashcards

Reactions for Quiz 1 Flashcards

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1
Q

Addition of NaNH2 and alkyl halide to an alkyne

A

Addition of carbons without breaking the triple bond

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2
Q

NaOet to an alkyl halide

A

Creation of zaitsev double bond (located on the most substituted carbons)

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3
Q

Addition of HBr to an alkene

A

Addition of Br via markovnikov

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4
Q

Addition of HBr and ROOR to an alkene

A

Addition of Br via anti markovnikov

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5
Q

Addition of t-BuOK (bulky base) to an alkyl halide

A

Creation of hoffman double bound (located on the least substituted carbons)

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6
Q

Addition of 1. TsCl, pyr and 2. NaOEt to an alcohol

A

Creation of zaitsev double bond

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7
Q

Addition of H3O+ to double bond

A

Creation of a markovnikov alcohol

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8
Q

Addition of concentrationed H2SO4 and Heat to an alcohol

A

creation of zaitsev double bond

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9
Q

Addition of 1. TsCl, pyr and 2. t-BuOK

A

creation of hoffman double bond

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10
Q

Addition of 1. BH3 THF and 2. H2O2, NaOH to a double bond

A

Addition of an anti-m alcohol

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11
Q

Addition of 1. Hg(OAc)2, H2O and 2. NaBH4 to an alkene

A

Addition of an markovnikov alcohol

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12
Q

Addition of H2, lindlar’s catalyst to an alkyne

A

Cis double bond (substituents are located on both sides)

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13
Q

Addition of Na, NH3 to an alkyne

A

Trans double bond (substituents are located across the bond)

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14
Q

Addition of H2, Pt to a double bond

A

Reduction to a single bond

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15
Q

Addition of 1. Br2, hv and 2. NaOEt to an alkane

A

Creation of a double bond

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16
Q

Addition of 1. Br2 / CCl4 and 2. xs NaNH2 and 3. H2O to an alkene

A

Creation of a triple bond

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17
Q

Addition of 1. O3 and 2. DMSO

A

Ozonolysis, double bond is cut to form two aldehydes

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18
Q

Addition of a strong base like NaH or LiH to an alcohol

A

Formation of an alkoxide ion

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19
Q

Pka of water

A

15.7

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20
Q

Pka of alcohols

A

Roughly 15.4

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21
Q

What base do you NOT use to form an alkoxide ion from an alcohol

A

NaOH. The conjugate base must have at least 2 units higher pka than the acid on the left

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22
Q

How does resonance affect acidity?

A

Increases acidity, lowers pka, because the conjugate base is resonance stabilized

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23
Q

How does induction affect acidity?

A

Increases acidity, lowers pka, because the negative charge of a conjugate base is stabilized by electron withdrawing groups

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24
Q

How does solvation effects affect acidity?

A

Decreases acidity, increases pka, because the conjugate base is harder to solvate making it less stable

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25
Q

Addition of a NaOH to a primary alkyl halide

A

Formation of a hydroxyl group but by the Sn2 reaction

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26
Q

Addition of water or NaOH to tertiary alkyl halide

A

Formation of a hydroxyl group but by the Sn1 reaction

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27
Q

Addition of water or NaOH to a secondary alkyl halide

A

Formation of hydroxyl group but by either the Sn1 reaction or the Sn2

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28
Q

Addition of dilute H2SO4 to a double bond (acid-catalyzed hydration)

A

markovnikov addition of an alcohol but there is the chance of a carbocation rearrangement

29
Q

Addition of 1. Hg(OAc)2, H2O and 2. NaBH4 to a double bond (oxymercuration-demurcuration)

A

markovnikov addition of an alcohol but no carbocation rearrangement

30
Q

Addition of 1. BH3 x THF and 2. H2O2, NaOH to a double bond (hydroboration - oxidation)

A

anti-markovnikov addition of an alcohol

31
Q

Addition of 1. MCPBA (RCO3H)and 2. H+ to a double bond

A

Trans addition of two alcohol groups

32
Q

Addition of catalytic OsO4 and NMO or KMnO4 and water to a double bond

A

Syn addition of two alcohol groups

33
Q

What is oxidation

A

increasing the bonds to heteroatoms

34
Q

What is reduction

A

decreasing the bonds to heteroatoms

35
Q

Pka of phenol

A

9.9

36
Q

Addition of 1. NaBH4 and 2. dilute acid to an aldehyde or ketone

A

Reduction of carbonyl to an alcohol group

37
Q

Addition of 1. LAH and 2. H2O to an aldehyde or ketone

A

Reduction of carbonyl to an alcohol group. Further reduces esters and carboxylic acids to a primary alcohol when adding two equivelents

38
Q

How to make a grignard reagent

A

Start with R-X, add Mg, use ether as a solvent to get R-Mg-X

39
Q

Addition of a 1. grignard reagent and 2. water to a carbonyl

A

Insertion of R group to the C that was bonded to Oxygen as well as turning the oxygen into an alcohol

40
Q

Addition of a grignard reagent and water (at the same time) to a carbonyl with an alcohol, amine, carboxylic acid

A

Nothing happens. No reaction when a slightly acidic proton is present

41
Q

Addition of 2 equivalents of grignard reagents and 2. water to an ester

A

Insertion of R group twice to the carbon bonded to both oxygens and formation of an alcohol where carbon double bond used to be

42
Q

How do you protect alcohols?

A

Addition of TMSCl and TEA

43
Q

How do you unprotect alchols

A

TBAF

44
Q

Addition of HBr to an alcohol

A

Replace hydroxyl with Br

45
Q

Addition of SOCl2 and pyr to an alcohol

A

Replace hydroxyl with Cl via Sn2, creation of SO2,

46
Q

Addition of PBr3 to an alcohol

A

Replace hydroxyl with Br via Sn2

47
Q

Addition of H3PO4 or H2SO4 and heat to an alcohol

A

Formation of an alkene

48
Q

Addition of 1. TsCl, pyr 2. NaOEt to an alcohol

A

Formation of an alkene

49
Q

Addition of POCl3 and heat to an alcohol

A

Formation of an alkene

50
Q

Addition of CrO3 and H+ or Na2Cr2O7 and H+

A

Formation of a carboxylic acid from a primary alcohol and formation of a ketone from a secondary alcohol

51
Q

Addition of PCC to a primary aldehyde

A

Secondary ketone

52
Q

Dess Martin Product

A

Primary aldehyde to a secondary ketone

53
Q

Addition of 1. DMSO, C2O2Cl2 2. TEA, Ch2Cl2 to an alcohol

A

Formation of an aldehyde (swern)

54
Q

How to name ethers

A

The larger -R group is the parent chain and the smaller -R group is the alkoxy substituent

55
Q

How to name an epoxide

A

oxygen is treated as a side group and two numbers are given as its locants

56
Q

Where is the peak for alcohol on IR

A

3600-3200 cm^-1

57
Q

Where do carbons of an alcohol show up in Carbon NMR

A

50-60

58
Q

Where does the proton of a hydroxyl on proton NMR show up

A

If it shows up, it’ll be around 3-4ppm

59
Q

Addition of H2SO4 to an alcohol

A

Can make a double bond or an ether where each side is symmetrical

60
Q

Williamson Ether Synthesis

A

Make an alkoxide from an alcohol (with something like NaH and LiH) and use the alkoxide as a nucleophine in Sn2 with alkyl halide to get an ether

61
Q

How to make an epoxide from an alkane with Cl and OH

A

Addition of NaOH, the OH deprotonates the alcohol and the alkoxide attacks the carbon bound to the chlorine

62
Q

Addition of 1. Hg (Co2CF3) ROH and 2. NaBH4 to an alkene

A

Markovnikov addition of OR group

63
Q

Addition of HI or HBr and Heat to an ether (opposite of williamson ether)

A

Ether turns back into an alcohol

64
Q

Addition of MCPBA to an alkene

A

Epoxide formation

65
Q

Addition of 1. Br2, H2O or NBS, H2O or HOCl and 2. NaOH to an alkene

A

epoxide formation

66
Q

Addition of H2SO4 and water to an epoxide

A

Opening of epoxide and formation of two OH (unless there is no water). Nucleophile attacks tertiary carbon if one is present. If not, attacks the less substituted carbon.

67
Q

What happens in base-catalyzed epoxide opening?

A

nucleophile always attacks least subtituted carbon via sn2.

68
Q

What are reagents that can be used in base-catalyzed epoxide opening

A

Br, OH, H2N-R, RS, N3, CN, H, R-MgBr

Organic Chemistry 2 (2 decks)

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