Exam 4 Flashcards

1
Q

Nomencalture

A

_ always have the double bond in the parent chain

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

Zusammen (Z)

A
  • Cis
  • Priorities are on the same side of the double bond
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

Entgegen (E)

A
  • Trans
  • Priorities are on opposite sides of the double bond
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

Synthesis of Alkenes

A

E1, E2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

H2, Pd/c, CH3OH

A

Alkyne to Alkane

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

H2, Lindlars catalyst

A

Alkyne to a cis alkene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Na, NH3

A

Alkyne to trans alkene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

H-X

A

Mark addition of a hydrogen and a halogen
1. H added to the less substituted carbon
2. Hydrid shift available for Br to attack

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

H-X, H2O2

A

anti mark addition of a hydrogen and a Br

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

X2

A

trans addition of two halogens
1. one br makes a bromonium ion
2. second br attacks below to release the first br up

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

X2, ROH

A

Trans and anti-mark (Br) addition of a halogen and a polar protic molecule
1. one br makes a bromonium ion
2. the polar protic molecule attacts the more substituted carbon releasing the Br
3. the second Br removes the extra hydrogen

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

H2SO4, H2O

A

mark addition of a hydrogen and a polar protic molecule (OH)
1. Acid donates a hydrogen
2. hydride or methyl shift
3. the polar protic solvent attacks the more substituted side
4. acid comes back to take off the extra hydrogen

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q
  1. Hg(OAC)2
  2. NaBH3
A

Mark addition of a hydrogen and an OH group

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q
  1. BH3, THF
  2. H2O2, NaOH
A

anti-mark addition of a hydrogen and an OH group

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q
  1. CH2N2, Light
  2. CH2I2, Zn, CuCl
A

makes a Carbene (:CH2)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

HCX3, NaOH

A

makes a carbene with halogens (:CX2)

17
Q

R-N3, light

A

makes a nitrene

18
Q

mCPBA

A

Makes an epoxide

19
Q

OsO4, H2O2

A

syn addition of two OH groups

20
Q

KMnO4 (Cold), H2O

A

Syn addition of two OH groups

21
Q
  1. mCPBA
  2. H2SO4, H2O
A

Trans addition of two Oh groups
1. acid adds a hydrogen to the epoxide
2. H2O attacks the bottom releasing the epoxide upwards
3. acid comes back to take the extra OH

22
Q
  1. KMnO4 (Warm/Hot)
  2. H3O+
A

Cleaves double and triple bonds, replacing them with a double bonded oxygen adn any lone hydrogens become an OH

23
Q
  1. O3
  2. (CH3)2-S
A

Cleaves double bonds and replaces it with a double bonded oxygen, Leaves lone Hydrogens alone

24
Q
  1. NaNH2
  2. R-Br
A

Makes the Alkyne chain longer
1. :NH2 removes the end hydrogen leaving the electrons
2. the electrons attach to the R group and kicks the Br off

25
KOH (2 equivalents)
Alkane to alkyne by removing hydrogens and halogens
26
1. NaNH2 (xs) 2. H3O+
able to move the triple bond from the center of the carbon to the end
27
KOH (xs)
able to move the triple bond to the center of the molecule
28
Alkyne: H-X
Mark and syn addition of a hydrogen and a halogen
29
Alkyne: X2
trans addition of two halogens
30
Alkyne: HgSO4, H2SO4, H2O
makes a ketone: 1. acid makes the mark product 2. a hydrogen from the acid attacks the remaining double bond the charge makes a double bond with the OH through resonance 3. the leftover acid takes the extra hydrogen back
31
1. (Sia)2BH 2. H2O2, NaOH
Alkyne to antimark Aldehyde
32
1. O3 2. H2O
Cleves the triple bond leaving a double bonded oxygen and an OH group