Sample Questions for Exam 3

1. The product, C, of the following sequence of reactions,

CH 3 CH 3 CCHO CH 3

+ CH 3CH 2CHO

OH-

H 3O + (-H2 O)

NaBH 4 CH3OH

would be: CH3 A)

CH 3CCH=CHCH2 CH 2OH CH 3 CH 3 CH 3CCH=CCH 2OH CH3 CH3 CH 3 CH 3CCH 2 CH 2CH2 OH CH3

D)

CH3 CH3 CCH2 CH2 CH 2CH 2OH CH 3 CH3 CH 3CCH2 CHCHO CH 3 CH3

B)

E)

C)

2. What would be the major product of the following reaction?

O C6 H 5CH=CHCCH 3

+ CN-

CH3CH 2OH CH3COOH

A)

O C6H5CH 2CHCCH 3

D)

O C6 H5 CH 2CH2 CCN

B)

CN O
C6 H5 CHCH 2CCH 3 CN

E)

OH C 6H5 CHCH=CCH 3 CN

C)

OH C6 H5 CH2 CH 2CCH 3 CN

Page 1

3. What would be the major product of the following reaction sequence?

O

i. LDA ii. C2H5I

O O

II
O

III

A) I

IV B) II

C) III

V D) IV

E) V

4. What synthetic strategy would accomplish the following transformation? ?

O O

A) B) C) D) E)

i) Br2 , H3 O+; ii) NaOC2 H5 , C2 H5 OH, heat i) Cl2 , FeCl3 ; ii) NaOC2 H5 , C2 H5 OH, heat i) HCN; ii) H3 O+, heat i) Br2 , h; ii) (CH3 )3 COK, (CH3 )3 COH, heat i) Br2 , H3 O+; ii) (CH3 )3 COK, (CH3 )3 COH, heat

5. Which of these is a product of the reaction of C6 H5 MgBr with

O C6 H5 CH=CHCCH 3 O A)

D)
p-C6 H5 C 6H 4

O CH=CHCCH 3

C6 H 5CH=CCCH 3 C 6H 5 OH
C6 H 5CH=CHCCH 3 C 6H 5 O

B)

E)

OC6 H5 C6 H5 CH=CHCHCH 3

C)

C6 H5 CH=CHCCH 2C 6H 5

Page 2

6. Which reagents would you use to synthesize this compound by an aldol condensation?
O C6 H5 CH=CHCC 6H 5 O
C6 H5 CH

A) B) C)

O C 6 H5 CH 2CH O

D) E)

O C6 H 5CCH 3

and
O

and

C6 H5 CH
O

C6 H5 CH 2CH

and
O

C6 H5 CCH 3

(C 6H5) 2CuLi and CH2 =CHCC 6H 5

C6 H5 CH=CHCH

and

C6H5OH

7. The aldol condensation product formed from 3-pentanone in the presence of base has the IUPAC name : A) 5-Ethyl-4-methyl-4-hepten-3-one D) 3-Ethyl-4-methyl-3-hepten-5-one B) 5-Ethyl-4-methyl-5-hepten-3-one E) 3-Ethyl-4-methyl-2-hepten-5-one C) 4-Methyl-4-nonen-3,7-dione

8. Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone? A) NaOI (I2 in NaOH) D) NaHCO3 /H2 O B) Br2 /CCl4 E) Ag(NH3 )2 + C) CrO 3 /H2 SO4

Page 3

9. The Robinson annulation reaction which produces

CH3 O

uses which of the following as starting materials?

H CH2=CHC=O

CH3

O CH2=CHCCH3

CH3

+
CH2

+
O

HCHO + III
O

I
O O

II

+
CH3CH=CHCCH3 O CH3CH=CHCCH3

+
O

A) I

B)

II

IV C) III

V
D) IV E) V

10. In which of the following sequences are the compounds listed in order of decreasing acidity? A) CH3 COOH > H2 O > CH3 CH2OH > HCCH > NH3 B) CH3 CH2 OH > CH3 COOH > H2 O > HCCH > NH3 C) CH3 COOH > CH3 CH2 OH > H2 O > NH3 > HCCH D) H2 O > CH3 COOH > CH3 CH2OH > HCCH > NH3 E) CH3 CH2 OH > H2 O > CH3 COOH > HCCH > NH3

11. Which of the following would be the strongest acid?

Cl CO2H Cl CO 2H Cl CO 2H Cl

I
CO 2H Cl

II
CO2H Cl Cl

III

A) I

IV B) II

C) III

V D) IV

E) V

Page 4

12. In which of these species are all the carbon-oxygen bonds of equal length? A) Diethyl carbonate D) Propionic anhydride B) Methyl butanoate E) Pentanoic acid C) Lithium acetate

13. A compound has the molecular formula C8 H14 O4 . Its IR spectrum shows a strong absorption band near 1740 cm-1 . Its 1 H NMR spectrum consists of: triplet, singlet, quartet, 1.3 2.6 4.2
O O O O O

The most likely structure for the compound is:

O O O O O O O

I
HO2C CO2H

II
O O O O

III

A) I

B)

II

IV C) III

D) IV

V E) V

14. Which of the reactions listed below would serve as a synthesis of acetophenone, C6 H5 COCH3 ? O A)
C6 H5 Cl O H3C Cl O + C 6 H6 + (CH 3 )2 CuLi

B) C)

AlCl 3

C6 H 5

+ CH3 MgI OCH3

D) Two of these E) All of these

15. Choose the reagent(s) that would bring about the following reaction: CH3 CH2 CH2CO2 CH3 CH3 CH2 CH2 CHO A) H2 /Ni D) NaBH4 , CH3 OH B) Li/liq NH3 E) LiAlH4 , ether C) LiAlH[OC(CH3 )3 ]3

Page 5

16. Which of the following is not a method for preparing butanoic acid? A) CH3 CH2 CH2 Br + NaCN; then H3 O+, reflux B) CH3 CH2 CH2 MgBr + CO2 ; then H3 O+ C) CH3 CH2 CH2OH + CO D) CH3 CH2 CH2CO2 Et + OH /H2 O; then H3 O+ E) CH3 CH2 CH2CH2 OH + KMnO 4 /OH /H2 O/heat; then H3 O+ 17. Which of the indicated hydrogens can be replaced by alkylation? (V)
H H S H3C H3C H S H (III) H H H H

(IV)

(II) (I) A) I B)

II

C) III

D) IV

E) V

18. What is the expected product from the following reaction sequence? O O O i. NaOC2H5, C2H5OH + ? O O + ii. H3O
O O O O O O O O O O O

I
O O O

II

III

A) I

B)

IV II C) III

D) IV

E) V

Page 6

19. The product(s) of the reaction of 2 mol of ethyl butanoate with sodium ethoxide is (are): O O A) D) O OH + NaOH
O

B) C)

O O

E)

O O

O O

20. Which reagents would be used in a Mannich reaction to synthesize

O N O

I
O

O H

+ (CH3) 2NH

II
O

O H

+ (CH3) 3N

III
O

+ (CH3)3N

+ base

IV
O

H H

+ (CH3) 2NH

V
A) I B)

+ (CH3) 2NH
II C) III D) IV E) V

21. Which organic reagents would you need to make 2-ethylheptanoic acid from diethyl malonate? A) Bromoethane, 1-bromopentane, sodium ethoxide, and potassium tert-butoxide B) 3-Bromooctane and sodium ethoxide C) 3-Bromoheptane and sodium ethoxide D) 1-Bromopropane, 2-bromopentane, sodium ethoxide, and potassium tert-butoxide E) 2-Bromoheptane and potassium tert-butoxide

Page 7

22. Which of the following statements is true of the enamine,

N:

A) The enamine can be made from cyclohexanone + pyrrolidine. + B)

N

It has another resonance structure : C) It can be acylated at the -carbon of the original carbonyl compound. D) It can be alkylated. E) All of the above are true.
:

23. Which of these is not a reversible process? A) Base-promoted ester hydrolysis D) Claisen condensation B) Acid-catalyzed ester hydrolysis E) Acetal formation C) Aldol addition

24. What final product is expected when toluene is subjected to the following reaction sequence? i) KMnO 4 , NaOH; ii) H3 O+ ( product = C7 H6 O2 ); iii) SOCl2 ; iv) NH3 (product = C7 H7 NO); v) Br2 , NaOH A) C6 H5 CONH2 D) p-CH3 C6 H4NH2 B) C6 H5 CH2 NH2 E) C6 H5NH2 C) p-CH3 C6 H4 SO2NH2

Page 8

25. What would be the product of the following reaction sequence?

Cl

i)

, AlCl3 ?

ii) (CH3)2NH iii) LiBH3CN

N O

O N N

I
OH

II

III

N N

A) I

B)

IV II

C) III

V D) IV

E) V

Page 9

Answer Key
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. B B A A B D A A B A C C A D C C C A C D A E A E C

Page 10