Prelim 2

Question 1

bromine addition- when there is an asymmetric double bond….

Answer 1

there are 2 possible products

Question 2

bromine addition- when one carbon has 2 alkyl substituents

Answer 2

• regioselective

- OH goes to carbon with greater alkyl substituents

Question 3

intermediate step of bromine addition (no excess water)

Answer 3

bromonium ion

Question 4

products of bromine addition (with excess water)

Answer 4

• bromohydrin
• H3O+
• Br-

Question 5

oxymercuration reduction

Answer 5

-HgOAC (fewer alkyl groups) and -OH groups (more alkyl groups) + HOAc
HgOAc replaced by H during reduction
- Markovnikov product

Question 6

catalysts used in oxymercuration reduction

Answer 6

• THF
• H2O
• NBH4
• NaOH

Question 7

intermediate in oxymercuration reduction

Answer 7

mercurinum ion

Question 8

hydroboration-oxidation

Answer 8

• B attaches to fewer alkyl groups
• B replaced by -OH during oxidation
• anti-Markovnikov

Question 9

reacts & catalysts in hydroboration-oxidation

Answer 9

• BH3
• THF
• H2O2
• NaOH

Question 10

ozonolysis reactants

Answer 10

O3 (one double bond, one single), O in middle has positive charge, O with single bond has negative charge

Question 11

O3 –> (CH3)2S

Answer 11

• break the double bond, double bond to oxygen instead of carbon
• ketone // aldehyde // formaldehyde

Question 12

O3 –> H2O2/H2O

Answer 12

• break the double bond, double bond to oxygen
• if hydrogen attached, turns ONE of the hydrogens into OH
• ketone // carboxylic acid // formic acid

Question 13

stereochemistry change in bromine addition

Answer 13

overall anti-addition

Question 14

stereochemistry change in hydroboration-oxidation

Answer 14

syn addition –> retention of configuration

Question 15

hydrogenation (Pd/C & H2)

Answer 15

syn addition

Question 16

stereochemistry change in oxymercuration-reduction

Answer 16

anti-addition –> retention + inversion of configuration