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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?

Study These Flashcards
A

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

22
Q

how do you make an alkene from a haloalkene?

Study These Flashcards
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?

Study These Flashcards
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?

Study These Flashcards
A

add POCl3 in pyridine -> E2

25
what does s-trans mean?
2 double bonds on opposite sides of a single bone
26
what does s-cis mean?
two double bonds on the same side of a single bond
27
what happens with electrophilic addition of a diene under warm conditions?
1,4 addition - rearranging of double bond after carbocation is formed
28
what happens with electrophilic addition of HX to a diene under cold conditions
1,2 addition
29
how do you make a common name for an alcohol?
alkyl group plus alcohol | C-OH = methyl alcohol
30
what is the common name for H-O-C-C-OH?
ethylene glycol
31
what is the common name for 1,2,3-propanetriol?
glycerol
32
how do you make anti markovnikov alcohol from alkene?
hydroboration BH3 - concerted reaction, OH replaces the BH2 | add BH3 plus OH- plus H2O2
33
how do you name an ether using IUPAC?
name longest chain as alkane, name O-R as branch -oxy (alkoxy)
34
what is furan?
pentagon with 2 double bonds and an O
35
what is 1,4-dioxane?
hexagon w/2 opposite O's
36
what is oxolane?
pentagon with an O
37
what is oxirane?
ethylene oxide | triangle with an O
38
how do you name an ether using common names?
name each alkyl group add ether
39
when synthesizing ethers using williamson synthesis, which one is the preferred R-X?
the least substituted one
40
what is ethoxide?
C-C-O-
41
what is propoxide?
C-C-C-O-
42
How do you make an ether from an alcohol?
add alkene and acid catalyst
43
How do you make an ether from an alkene?
add alcohol and a catalyst
44
alkene + alcohol + acid catalyst
ether
45
what is mineral acid catalyzed cleavage of an ether?
R-O-R + 2HX-> 2RX + H2O primary is Sn2 secondary and tertiary are Sn1
46
R-O-R + 2HX=?
2RX + H2O
47
how do you name an epoxide using IUPAC?
parent is oxirane, branches off ring (2 and 3) | OR epoxy branch numbering attachment parts (2,3 epoxy)...
48
How do you name an epoxide using common names?
name it as if it were an alkene, add oxide to end
49
what is oxidation?
loss of C-H bonds
50
alkene plus peroxyacid CH3COOOH
epoxide where the double bond was + CH3COOH
51
alkene + H2O
alcohol - Markovnikov

Organic Chemistry (6 decks)

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