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Organic Chemistry > exam 1 > Flashcards

exam 1 Flashcards

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1
Q

epoxide + H2O and H+ (H2SO4)

A

beta diol

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2
Q

how do you make a beta diol from an epoxide?

A

add H2O and acid (H2SO4)

nucleophile attacks more substituted

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3
Q

epoxide + HX

A

beta halohydrin X-C-C-OH

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4
Q

how do you make a halohydrin from an epoxide?

A

add HX

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5
Q

epoxide + 1) -OR 2)H2O

A

alkoxyalcohol C-O-C-C-OH

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6
Q

how do you make an alkoxyalcohol from an epoxide?

A

1) -OR

2) H2O

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7
Q

how do you make an alkynyl alcohol from an epoxide?

A

1)RCtripleC- 2)H2O Sn2 reaction -> CtripleC-C-C-OH

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8
Q

epoxide + 1)RCtripleC- 2)H2O

A

alkynyl alcohol CtripleC-C-C-OH

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9
Q

how do you make a beta diol from an epoxide?

A

1)OH- 2)H2O sn2 OH-C-C-OH

nucleophile attacks less substituted C

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10
Q

What do you get when you add 1)OH- 2)H2O to an epoxide?

A

beta diol

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11
Q

epoxide + strong nucleophile (-OH, -OR, -CN, -SR, NH3) + H20

A

nucleophile attacks less substituted C, H2O protonates the O Nu-C-C-OH
nucleophile attacks from the back

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12
Q

epoxide with acid (HCl, HBr, H2O + acid, ROH + acid)

A

1)protonation of epoxide O to make good leaving group
2) nucleophile Z- opens ring by backside attack
nucleophilic attack occurs at more substituted C

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13
Q

alcohol + HX

A

RX + H2O
secondary and tertiary, Sn1 + rearrangement
primary, Sn2

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14
Q

How do you make an RX from an alcohol?

A

add HX

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15
Q

alcohol + SOCl2 in pyridine

A

R-Cl Sn2 with primary and secondary ROH

doesn’t work with tertiary

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16
Q

how do you get an Sn2 reaction with a primary alcohol to form an RX?

A

add SOCl2 in pyridine

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17
Q

How do you make an alkoxide salt?

A

ROH + NaH -> RO- Na+ + H2

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18
Q

How do you make an ether?

A

haloalkane + RO- sn2 reaction

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19
Q

haloalkane + RO-

A

ether

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20
Q

alcohol + strong acid (H2SO4)

A

alkene
secondary and tertiary alcohol->E1 rearrangement
primary, E2

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21
Q

How do you make an alkene from an alcohol?

A

add strong acid (H2SO4)
secondary or tertiary alcohol=E1 & rearrangement
primary = E2

22
Q

how do you make an alkene from a haloalkene?

A

primary strong bulky base (E2)
secondary strong base (E2 and SN@)
tertiary strong base (E2), weak base (E1)

23
Q

how do you make an alkene from an alcohol?

A

dehydration with H2SO4 (acid) (SN1 for secondary and tertiary, SN2 for primary)
add heat to go backwards
Zaitsev

24
Q

How do you make an alkene from an alcohol with no rearrangement?

A

add POCl3 in pyridine -> E2

25
Q

what does s-trans mean?

A

2 double bonds on opposite sides of a single bone

26
Q

what does s-cis mean?

A

two double bonds on the same side of a single bond

27
Q

what happens with electrophilic addition of a diene under warm conditions?

A

1,4 addition - rearranging of double bond after carbocation is formed

28
Q

what happens with electrophilic addition of HX to a diene under cold conditions

A

1,2 addition

29
Q

how do you make a common name for an alcohol?

A

alkyl group plus alcohol

C-OH = methyl alcohol

30
Q

what is the common name for H-O-C-C-OH?

A

ethylene glycol

31
Q

what is the common name for 1,2,3-propanetriol?

A

glycerol

32
Q

how do you make anti markovnikov alcohol from alkene?

A

hydroboration BH3 - concerted reaction, OH replaces the BH2

add BH3 plus OH- plus H2O2

33
Q

how do you name an ether using IUPAC?

A

name longest chain as alkane, name O-R as branch -oxy (alkoxy)

34
Q

what is furan?

A

pentagon with 2 double bonds and an O

35
Q

what is 1,4-dioxane?

A

hexagon w/2 opposite O’s

36
Q

what is oxolane?

A

pentagon with an O

37
Q

what is oxirane?

A

ethylene oxide

triangle with an O

38
Q

how do you name an ether using common names?

A

name each alkyl group add ether

39
Q

when synthesizing ethers using williamson synthesis, which one is the preferred R-X?

A

the least substituted one

40
Q

what is ethoxide?

A

C-C-O-

41
Q

what is propoxide?

A

C-C-C-O-

42
Q

How do you make an ether from an alcohol?

A

add alkene and acid catalyst

43
Q

How do you make an ether from an alkene?

A

add alcohol and a catalyst

44
Q

alkene + alcohol + acid catalyst

A

ether

45
Q

what is mineral acid catalyzed cleavage of an ether?

A

R-O-R + 2HX-> 2RX + H2O
primary is Sn2
secondary and tertiary are Sn1

46
Q

R-O-R + 2HX=?

A

2RX + H2O

47
Q

how do you name an epoxide using IUPAC?

A

parent is oxirane, branches off ring (2 and 3)

OR epoxy branch numbering attachment parts (2,3 epoxy)…

48
Q

How do you name an epoxide using common names?

A

name it as if it were an alkene, add oxide to end

49
Q

what is oxidation?

A

loss of C-H bonds

50
Q

alkene plus peroxyacid CH3COOOH

A

epoxide where the double bond was + CH3COOH

51
Q

alkene + H2O

A

alcohol - Markovnikov

Organic Chemistry (6 decks)

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