Exam 2

Question 1

what products can primary alcohols form

Answer 1

haloalkanes, terminal alkenes, carboxylic acids, aldehyde, ethers

Question 2

what products can secondary alcohols form

Answer 2

haloalkane, substituted group, internal alkene, ketone, ethers (regular or cyclic)

Question 3

what products can tertiary alcohols form

Answer 3

haloalkanes, internal alkenes

Question 4

what products can tertiary ethers form

Answer 4

alcohol

Question 5

what products can allylic and benzylic ethers form

Answer 5

alcohols

Question 6

what can a 1,2-difunctionalized compound form

Answer 6

alcohol with a different functional group

Question 7

what can a halohydrin form

Answer 7

epoxide

Question 8

what can an alkene form

Answer 8

epoxide

Question 9

what can an epoxide form

Answer 9

1,2-difunctionalized group

Question 10

what can an alkyl halide form

Answer 10

an alkyl grignard reagent, an organolithium reagent and a 1,2-difunctionalized group

Question 11

what can an aryl halide form

Answer 11

an aryl grignard reagent

Question 12

what reactions can a binary acid cause

Answer 12

• conversion of ROH –> haloalkane
• acidic acid cleavage

Question 13

what reactions can PBr3 cause

Answer 13

ROH –> haloalkane

Question 14

what reaction can SoCl2 cause

Answer 14

ROH –> haloalkane

Question 15

what reaction can TsCl, pyr, and nucleophile cause

Answer 15

ROH –> aryl/alkyl sulfonates

Question 16

what reactions can an oxyacid (hydronium) cause

Answer 16

acid-catalyzed dehydration, epoxide ring opening

Question 17

what reactions can K2Cr2O7/H2SO4 cause

Answer 17

oxidation of primary or secondary alcohol

Question 18

what reactions can CrO3/H2SO4 cause

Answer 18

oxidation of primary or secondary alcohol

Question 19

what reactions can KMnO4/OH-/heat cause

Answer 19

oxidation of primary or secondary alcohols

Question 20

what reactions can PCC/CH2Cl2 cause

Answer 20

• partial oxidation of primary alcohol –> aldehyde
• oxidation of secondary alcohol –> ketone

Question 21

what reactions does a strong base and an electrophile cause

Answer 21

Williamson ether synthesis

Question 22

what reaction does TMSCl or ROTMS cause

Answer 22

protection of OH-

Question 23

what reaction does MCPBA cause

Answer 23

epoxidation of alkene

Question 24

what reaction does Mg and an ether cause

Answer 24

preparation of organomagnesium compound

Question 25

what reaction does 2Li and pentane cause

Answer 25

preparation of organolithium reagent

Question 26

what reaction does Grignard’s reagent cause

Answer 26

ring opening of epoxide

Question 27

what reactions does Gilman’s reagent cause

Answer 27

• ring opening of epoxide
• substitution of alkyl halide

Question 28

what reactants do you need to form a haloalkane

Answer 28

• any alcohol

Question 29

what reactant do you need to form a terminal alkene

Answer 29

primary alcohol

Question 30

what reactant do you need to form an internal alkene

Answer 30

secondary/tertiary

Question 31

what reactant do you need to form a carboxylic acid

Answer 31

primary alcohol

Question 32

what reactant do you need to form a ketone

Answer 32

secondary alcohol

Question 33

what reactant do you need to form an aldehyde

Answer 33

primary alcohol

Question 34

what reactants do you need to form an ether

Answer 34

alcohols

Question 35

what reactants do you need to form an alcohol with a single functional group

Answer 35

• tertiary, allylic, and benzylic ethers

Question 36

what reactants do you need to form an epoxide

Answer 36

halohydrin, alkene

Question 37

what reactants do you need to form a 1,2-difunctionalized alcohol

Answer 37

epoxide

Question 38

what reactants do you need to form Grignard’s reagent

Answer 38

alkyl/aryl halide

Question 39

what reactant do you need to form an organolithium reactant

Answer 39

alkyl halide