ochem

Question 1

HCl or HBr

Answer 1

adds Cl or Br to double bond

markovnikov

Question 2

1. Hg(OAc)2, H2O, THF,
2. NaBH4, NaOH

Answer 2

adds an OH

markovnikov

needs a double bond, no carbon shifts

Question 3

Cl2, CCl4

Answer 3

adds 2 Cl anti, makes a little triangle intermediate

Question 4

Br2, CH2Cl2

Answer 4

anti addition of Br, makes little triangle

Question 5

Br2, H2O

another ex: Cl2, HOCH3

Answer 5

halogen adds antimarkovnikov, OH adds markovnikov

no carbon shifts

Question 6

HBR, ROOR

or CH3CH2OOCH3 or H2O2 (also are roor)

Answer 6

anti markovnikov reaction

Question 7

Epoxide opening

Answer 7

ACID: most substituted site

BASE: least substituted site

Question 8

O3, Zn/H2O

Answer 8

cleaving, adds a =O

Question 9

H2, PdC

Answer 9

syn addition of Hydrogens

can bring double AND triple bonds to single ones

Question 10

H2, Lindlars

Answer 10

CIS reduction from alkyne to alkene

Question 11

Li, NH3

Answer 11

TRANS reduction from alkyne to alkene

Question 12

HgSO4, H2SO4

Answer 12

adds a ketone to an internal alkyne

markovnikov

Question 13

1. BH3, THF
2. H2O2, OH-, H2O

Answer 13

first, a BH2 adds antimarkovnikov.

then it switches with a OH

then TAUTOMERIZATION changes the OH to a =O

“Hydroboration-oxidation results in the anti-Markovnikov addition of a hydroxyl group to alkenes”

Question 14

1. OsO4, Pyridine
2. NaHSO3, H2O

Answer 14

SYN addition of 2 OH

forms a biggie fatty intermediate but I dont care

Question 15

NaNH2

Answer 15

strips proton, a common example is making alkenes have a negative charge to kick up the crotch

• Dr ari

Question 16

H2SO4, H2O

Answer 16

markovnikov addition of OH

can carbon shift

Question 17

Br2, hv

Answer 17

one halogen as added, big radical rxn takes place

NOTE: Br attaches at the most substituted carbon, while Cl adds to wherever

Question 18

NBS

Answer 18

NBS (N-BromoSuccinimide) is a mild, radical brominating reagent. NBS adds a bromine to the carbon that is one position away from the double bond (the allylic carbon)

Question 19

KMnO4, OH-, H3O+ hv

or

Na2Cr2O7, H2SO4

Answer 19

needs a benzylic hydrogen, turns that area (carbon) into a COOH

Question 20

Br2, FeBr3

Answer 20

EAS, must look a the group on the product to determine orthopara OR meta.

Typically, in ortho para, PARA is the winner

EAS love rearranging esp carbons

Question 21

1. H2NNH2
2. KOH, hv

Answer 21

removes =O

Question 22

Zn(Hg), HCl, Hv

Answer 22

removes =O

Question 23

1. CuCN
2. H3O+, hv

Answer 23

STEP 1, adds CN

STEP 2, COOH

Question 24

Na2Cr2O7, H3O+

Answer 24

primary alcohols to COOH

secondary alcohols to =O

Question 25

NaOEt, HOEt

Answer 25

removes halogen, adds double bond

Question 26

MCPBA

Answer 26

makes O epoxide

Question 27

PCC

Answer 27

The reagents oxidize primary alcohols to aldehydes.

Question 28

KMnO4

Answer 28

primary alcohols to COOH

Question 29

NaBH4

Answer 29

reduces aldehydes and ketones to alcohols