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1

2

What is the mechanism for nucleophilic addition under basic conditions?

3

What is the mechanism for nucelophilic addition under acidic conditions?

4

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

(Ph)CH=CH2

5

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

 

1. LiAlH4
2. H3O+

6

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

Bromobenzene

1. Mg, Et2O
2. Ethylene oxide (epoxide)
3. H3O

7

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

2-Heptanol

Note: You can make the necessary epoxide by dehydration of propanol followed by oxidation with m-CPBA.

8

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

1-Butanethiol

9

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

 2-Hexanol

10

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

 2-Hexanone - CH3CO(CH2)3CH3

1. PBr3
2. Mg, Et2O
3. Acetaldehyde
4. H3O+
5. CrO3, aq. H2SO4

11

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

2-Methyl-1,2-propanediol

12

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

2,2-Dimethylpropanal - (CH3)3CCHO

13

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less. 

 

Hexanoic acid - CH3(CH2)4CO2H

14

Dess Martin Reaction (Periodinane)

15

Give reagents that accomplish the following transformation.

1. PBr3
2. ((CH3)2CH)2CuLi   Gilman reagent

16

Give reagents that accomplish the following transformation.

1. H2, Lindlar's Catalyst
2. O3; Zn, H3O+

17

Give reagents that accomplish the following transformation.

1. BH3, THF
2. H2O2, aq. NaOH
3. NaH
4. CH3CH2CH2Br

18

Give reagents that accomplish the following transformation.

1. NaOtBu, tBuOH
2. mCPBA
3. NaOMe, MeOH
4. NaH; MeI

19

What happens when you react TMSO with PCC?

 

 

Compound A is oxidized using PCC and then reacted with methyl magnesium bromide,
CH3MgBr, to form Compound B.

 

http://pages.towson.edu/jdiscord/www/332_answer_keys/Chapters_17_and_19/PracticeExam1AnsKey.pdf

20

What are the reagents used to protect an alcohol before reacting Grignards?

 

How do you unprotect it after the reaction?

Protect with: 1. Me3SiCl, Et3N

 

De-protection: H3O+

21

How do you reduce a ketone or aldehyde into an alkane?

(Clemmenson Reaction)

Zn(Hg)/
HCl, H2O

22

What is the product?

23

What is the mechanism for cis diol formation from and alkene?

24

What is the reagent for cleaving an expoxide to yield trans diols?

25

What reagents cleave an epoxide to yield cis diols?

26

How do you reduce esters to alcohols?

27

How do you add Br to the benzylic position a the end of CH3 in Ph-CH3?

28

29

Claisen rearrangement followed by Diels-Alder

Tautomerization of the Claisen product to a phenol does not take place because no H is available to dontate to the Oxygen.

30