Practice Ex 3

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
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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
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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
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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
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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
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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
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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
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Practice Ex 3

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Sample Questions for Exam 3

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

would be: CH3 A)

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

CH3CH 2OH CH3COOH

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

i. LDA ii. C2H5I

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

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

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

9. The Robinson annulation reaction which produces

uses which of the following as starting materials?

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

The most likely structure for the compound is:

+ CH3 MgI OCH3

D) Two of these E) All of these

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

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

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

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

ii) (CH3)2NH iii) LiBH3CN

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