Exam 4

Question 1

Nomencalture

Answer 1

_ always have the double bond in the parent chain

Question 2

Zusammen (Z)

Answer 2

• Cis
• Priorities are on the same side of the double bond

Question 3

Entgegen (E)

Answer 3

• Trans
• Priorities are on opposite sides of the double bond

Question 4

Synthesis of Alkenes

Answer 4

E1, E2

Question 5

H2, Pd/c, CH3OH

Answer 5

Alkyne to Alkane

Question 6

H2, Lindlars catalyst

Answer 6

Alkyne to a cis alkene

Question 7

Na, NH3

Answer 7

Alkyne to trans alkene

Question 8

H-X

Answer 8

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

Question 9

H-X, H2O2

Answer 9

anti mark addition of a hydrogen and a Br

Question 10

X2

Answer 10

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

Question 11

X2, ROH

Answer 11

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

Question 12

H2SO4, H2O

Answer 12

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

Question 13

1. Hg(OAC)2
2. NaBH3

Answer 13

Mark addition of a hydrogen and an OH group

Question 14

1. BH3, THF
2. H2O2, NaOH

Answer 14

anti-mark addition of a hydrogen and an OH group

Question 15

1. CH2N2, Light
2. CH2I2, Zn, CuCl

Answer 15

makes a Carbene (:CH2)

Question 16

HCX3, NaOH

Answer 16

makes a carbene with halogens (:CX2)

Question 17

R-N3, light

Answer 17

makes a nitrene

Question 18

mCPBA

Answer 18

Makes an epoxide

Question 19

OsO4, H2O2

Answer 19

syn addition of two OH groups

Question 20

KMnO4 (Cold), H2O

Answer 20

Syn addition of two OH groups

Question 21

1. mCPBA
2. H2SO4, H2O

Answer 21

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

Question 22

1. KMnO4 (Warm/Hot)
2. H3O+

Answer 22

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

Question 23

1. O3
2. (CH3)2-S

Answer 23

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

Question 24

1. NaNH2
2. R-Br

Answer 24

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

Question 25

KOH (2 equivalents)

Answer 25

Alkane to alkyne by removing hydrogens and halogens

Question 26

1. NaNH2 (xs)
2. H3O+

Answer 26

able to move the triple bond from the center of the carbon to the end

Question 27

KOH (xs)

Answer 27

able to move the triple bond to the center of the molecule

Question 28

Alkyne: H-X

Answer 28

Mark and syn addition of a hydrogen and a halogen

Question 29

Alkyne: X2

Answer 29

trans addition of two halogens

Question 30

Alkyne: HgSO4, H2SO4, H2O

Answer 30

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

Question 31

1. (Sia)2BH
2. H2O2, NaOH

Answer 31

Alkyne to antimark Aldehyde

Question 32

1. O3
2. H2O

Answer 32

Cleves the triple bond leaving a double bonded oxygen and an OH group