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Organic chemistry > Exam 3 Sebahar > Flashcards

Exam 3 Sebahar Flashcards

1
Q

What is important to remember about E2?

A

Anti peri planar arrangement of H and X

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2
Q

Alkene + McPBA?

A

Epoxide

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3
Q

Alcohol + H2SO4 or H30+ and Heat

A

Alkene

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4
Q

Alcohol + POCl3, py

A

Alkene (E2)

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5
Q

Alcohol + HX

A

RX + H2O, protonate the alcohol, creates a leaving group and then water comes in.

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6
Q

Alcohol + SOCl2, py

A

R-Cl with inversion of stereochemistry

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7
Q

Alcohol + PBr3

A

R-Br with Inversion of Stereochemistry

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8
Q

Alcohol + TsCl, py

A

R-OTs with retention of stereochemistry

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9
Q

R-O-R + HX (2 equivalents)

A

R-X + R-X + H2O (Cleavage)

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10
Q

Epoxide + Nucleophile (basic conditions)

A

Nucleophile attacks the less substituted side

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11
Q

Epoxide + Acidic Conditions

A

Z (conjugate base) attacks the more substituted side

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12
Q

Alkene + HX

A

H bonds to less substituted carbon, syn and anti

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13
Q

Alkene + H2SO4, H2O

A

H bonds to less substituted carbon, syn and anti addition

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14
Q

Alkene + H2SO4, HOR

A

H bonds to the less substituted carbon, syn and anti addition, OR on one side instead of OH

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15
Q

Alkene + X2

A

Anti Addition

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16
Q

Alkene + X2, H2O

A

X bonds to the less substituted Carbon, anti addition occurs

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17
Q

Alkene + BH3 or 9BBN, H2O2, -OH

A

OH bonds to the less substituted carbon, syn addition only

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18
Q

Alkyne + HX (2 equivalents)

A

The halogens bond to the same carbon and the hydrogens bond to the same carbon.

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19
Q

Alkyne + X2 (2 equivalents)

A

halogens bond and saturate both carbons. Bridged halonium ions formed as intermediates

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20
Q

Alkyne + H2O, H2SO4, HgSO4

A

ENOL which changes into a KETONE

21
Q

Alkyne + BH3, H2O2, -OH

A

ENOL to an ALDEHYDE

22
Q

Alkene + H2, Pd/C or other Metal/C

A

Alkane

23
Q

Alkyne + 2 H2, Pd/C

A

Alkane

24
Q

Alkyne + H2, Lindlar’s Catalyst

A

Cis Alkene, syn addition

25
Q

Alkyne + Na, NH3

A

Trans Alkene , anti addition

26
Q

IR Aromatic Ring

A

Two peaks, 1500 and 1600

27
Q

Alkene

A

1650

28
Q

Carbonyl

A

1700

29
Q

Alkyne

A

2100

30
Q

Alkane

A

2900

31
Q

Terminal Alkyne

A

3300

32
Q

Carboxylic Acid O-H

A

2400-3000, very broad and irregular

33
Q

Alcohol, amine, amide IR

A

3200-3400 Broad, regular

34
Q

Alcohol NMR

A

Between 2-5 but broad

35
Q

Aromatic Ring NMR

A

7

36
Q

Amide NMR

A

10

37
Q

Aldehyde and Carboxylic Acid NMR

A

11

38
Q

KOt-Bu

A

E2. It will grab the least substituted Hydrogen

39
Q

R-X (alkyl halide) + LAH, H20

A

R-H (Alkane)

40
Q

Epoxide + LAH, H20

A

Alcohol. SN2 mechanism, LAH attacks the less substituted side.

41
Q

Alkene + 1. RCO3H, 2. H2O

A

1,2 diol. Epoxide ring intermediate, Anti addition

42
Q

Alkene + 1. OsO4, 2. NaHSO3, H2O or 1. OsO4, NMO, 2. NaHSO3, H20 or KMnO4, H2O, -OH

A

1,2 diol. Syn addition

43
Q

Alkene + 1. O3 2. Zn, H2O, CH3SCH3

A

Ketone + Aldehyde
Ketone + Ketone
Aldehyde + Aldehyde

44
Q

Internal Alkyne + 1. O3, 2. H20

A

cleaves into 2 Carboxylic acids

45
Q

Terminal Alkyne + 1. O3, H2O

A

Cleaves into 1 Carboxylic acid and CO2

46
Q

Primary Alcohol + PCC

A

Aldehyde

47
Q

Primary Alcohol + CrO3, H2SO4, H20

A

Carboxylic Acid

48
Q

Secondary Alcohol + PCC or CrO3

A

Ketone

49
Q

Alkene + 1. O3, 2. H2O2, NaOH, H2O

A

Carboxylic Acid (replace H with OH) and Ketone

Organic chemistry (6 decks)

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