CHEM 31 PROBLEM SET: ORGANIC MECHANISMS - NUCLEOPHILIC

NAME: _________________________________
1. Which one of the Grignard reactions below could give rise
to CH3CH2CH(OH)CH2CH3?
(A)
(B)
(C)
(D)

propanone and methyl Grignard

butyl Grignard and acetaldehyde
ethyl Grignard and propionaldehyde
methyl ethyl ketone and methyl Grignard

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

out the transformation shown below:
?
O
1,6-hexanedione

SEC. _______________

SCORE: ____________

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

H+
O + 2 CH 3OH

(A)
(B)
(C)
(D)
(E)

5,5-dimethyl pentanal
cyclopentanone dimethyl ketal
3-methyl-1,5-pentanedione
2-methyl cyclopentanone
cyclopentane dimethyl acetal

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

(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?
O
C (CH2) 4CH3
H 2NNH 2

KOH
heat

OH
CH (CH 2)3CH 3

(A)

(CH2) 4CH3

(D)
OH
CH (CH 2)4CH 3

(B)

(CH2) 5CH3

(E)
OCH 2 (CH 2)4CH 3

(C)
4. Which of the following reactions will produce a secondary
amine?

7. The saponification of the optically active ester using

isotopically labeled oxygen as shown above would most likely
produce which of the following products?

11. Of the following, which reacts with methylamine

(CH3NH2) to form the imine shown above?
8. Which of the following is a product of the reaction
sequence shown above?

12. Which of the following correctly indicates the order of

reactivity of the halides above with sodium iodide in acetone?

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?

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 + HCOO23. PhCOCH2CH3 + H2NNH2, OH- PhCH2CH2CH3
24. 2 CH3CHO + KOH/H2O CH3CH(OH)CH2CHO
25. CH3COOCH2CH3 + CH3CH2O-Na+
CH3COCH2COOCH2CH3