CHEM 31 PROBLEM SET: ORGANIC MECHANISMS - NUCLEOPHILIC

NAME: _________________________________ SEC. _______________ SCORE: ____________

1. Which one of the Grignard reactions below could give rise

to CH3CH2CH(OH)CH2CH3?

(A) propanone and methyl Grignard

(B) butyl Grignard and acetaldehyde

(C) ethyl Grignard and propionaldehyde

(D) methyl ethyl ketone and methyl Grignard

2. Indicate the reagents and/or compounds required to carry

out the transformation shown below:

(A) H2O; H2SO4, heat; KMnO4; O3; Zn

(B) LiAlH4; K2Cr2O7, H2O; NH2OH

(C) LiAlH4; NaOH, heat; KMnO4

(D) H2O, H+; K2Cr2O7; NH2OH

(E) LiAlH4; H2SO4, heat; O3; Zn

3. Which of the compounds below is the product of the

following reaction?

(A) (D)

(B) (E)

(C)

4. Which of the following reactions will produce a secondary

amine?

5. What is the principal product of the following reaction?

(A) 5,5-dimethyl pentanal (B) cyclopentanone dimethyl ketal

(C) 3-methyl-1,5-pentanedione

(D) 2-methyl cyclopentanone

(E) cyclopentane dimethyl acetal

6. What is the major product of the reaction shown above?

7. The saponification of the optically active ester using

isotopically labeled oxygen as shown above would most likely

produce which of the following products?

O?

1,6-hexanedione

C

O

(CH2)4CH3

H2NNH2

KOH

heat

CH

OH

(CH2)3CH

3(CH

2)4CH

3

CH

OH

(CH2)4CH

3(CH

2)5CH

3

OCH2

(CH2)4CH

3

O + 2 CH3OHH+

8. Which of the following is a product of the reaction

sequence shown above?

9. Which of the following structures is an intermediate formed

in the amide hydrolysis shown above?

10. What is the major product of the reaction shown above?

11. Of the following, which reacts with methylamine

(CH3NH2) to form the imine shown above?

12. Which of the following correctly indicates the order of

reactivity of the halides above with sodium iodide in acetone?

13. Which of the following reactions would NOT be an

acceptable method for the preparation of methyl benzoate?

14. Which of these reagents can accomplish the following

reaction?

A. NaBH4

B. LiAlH4

C. NaH

D. H3O+

15. Which of the following is an intermediate formed in the

reaction below?

A. C.

B. D.

16-20: Determine the type of reaction: Choose : A. Nucleophilic Substitution

B. Nucleophilic Addition

C. Electrophilic Substitution D. Electrophilic Addition

E. Free Radical Substitution

F. Elimination

G. Rearrangement

16. formation of hemiacetal

17. oxymercuration of styrene 18. conversion of allyl phenyl ether to o-allylphenol

19. reduction of acetaldehyde by NaBH4

20. acid hydrolysis of acetonitrile

21-25: Identify the type of reaction:

Choices: A. Clemmensen reduction

B. Wolf-Kishner reduction C. Aldol Condensation

D. Cannizzaro reaction

E. Claisen Condensation

21. C6H5CH2CHO + Zn(Hg), HCl C6H5CH2CH3

22. HCHO + PhCHO + OH- PhCH2OH + HCOO

-

23. PhCOCH2CH3 + H2NNH2, OH- PhCH2CH2CH3

24. 2 CH3CHO + KOH/H2O CH3CH(OH)CH2CHO

25. CH3COOCH2CH3 + CH3CH2O-Na+

CH3COCH2COOCH2CH3