Organic Chemistry 2

1. Which of the following compounds would NOT be 10. What is the position of the substituent after the
considered aromatic? nitration of benzoic acid?
a. Para position
b. Either ortho or para position
c. Meta position
d. Ortho position
a. c.
11. A primary alcohol under the reagent sodium dichromate
under acidic condition and water produces which of
the following?
a. An aldehyde c. A carboxylic acid
b. d. b. A ketone d. A quinone

2. Which among the choices is NOT aromatic? 12. What is the reactant needed to produce 3-methyl-2-
pentene when reacted with hot sulfuric acid?
H H a. 2-pentyne c. 3-methyl-2-pentanone
b. 3-methyl-2-pentanol d. 3-methylpentanal

For numbers 13-15, consider the following:

a. c.
H a. 2-pentanol c. 3-methyl-3-pentanol
b. 2-methyl-1-pentanol d. None of the above
13. Which alcohol would react quickly with Lucas reagent
(equimolar amounts of HCl and ZnCl2)?
14. Which alcohol would be oxidized to an aldehyde upon
b. d. reacting with a weak oxidizing agent?
15. Which alcohol would be oxidized to a ketone upon
3. Which of the following is/are characteristics of an reaction with Jones reagent?
aromatic compound?
I. It is cyclic and planar. 16. What is the IUPAC name of the product from the
II. It is completely conjugated. reaction given?
III. It is composed of even-numbered carbon atoms.
HBr
a. I only c. I and III ???
0°C
b. I and II d. I, II and III
a. 3-methyl-2-hexene c. 3-methyl-3-hexene
4. Which of the following substituents is NOT an ortho- b. 3-bromo-3-methylhexane d. 3-methylhexane
para director in an EAS reaction?
a. -Cl c. -OH 17. Which R group would complete the Grignard reaction
b. -NO2 d. -CH3 given?

5. Which of the following describes the effect of a

nitro group (-NO2) as a substituent in EAS? (i) RMgBr
a. Weakly activating, meta directing
b. Strongly deactivating, meta directing (ii) H+/H2O
c. Strongly activating, ortho-para directing
d. Weakly deactivating, ortho-para directing a. Sec-butyl c. propyl
b. Butyl d. isopropyl
6. What is the major organic product from the following
reaction? 18. What is the product when 2-propanol reacts with
sodium dichromate in acidic condition?
a. Propanone c. Propanoic acid
HNO3 b. Propanal d. Ethanoic acid
???
H2SO4
19. Which of the following will be useful to determine
a. m-nitrotoluene only c. o-nitrotoluene only the aromaticity of a compound?
b. p-nitrotoluene only d. o-nitrotoluene and a. 4n + 2 c. 4n + 2π
p-nitrotoluene b. n = 2π/4n d. n = 4n + 2

7. What reacts with benzene to produce a benzoic acid? 20. How many π electrons are present in the given
a. CH3Cl with AlCl3 and hot KMnO4 with water under compound?
acidic condition
b. CH3Cl with AlCl3 and excess NBS
c. CH3Cl with AlCl3 and hot Zn(Hg) in acidic
condition
d. Ethanoic acid with AlCl3
a. 4 c. 8
8. What is the first step in producing 4- b. 10 d. 12
bromobenzonitrile from benzene?
a. Nitration the reduction using Fe or Zn 21. The reaction given proceeds to form which of the
b. Nitration following?
c. Acylation then bromination O O
d. Bromination
OH 1) LAH, ether
9. What is the last step in producing 4-bromo-2- ???
nitrotoluene from benzene? 2) H2O
a. Bromination
b. Nitration a. Two carboxylic acid group
c. Friedel-Crafts alkylation b. An aldehyde and a ketone
d. Friedel-Crafts acylation c. A diol
d. An aldehyde to the carboxylic acid substituent

Prepared by: Engr. Quennie Marie L. Bañares

 Organic Chemistry 2
22. The reaction given proceeds to form which of the 29. Which of the following is the product from the
following? reaction given?

OH PCC (1) EtMgBr

??? ???
CH2Cl2 (2) H2O

HO a. 2-methylpentanol c. 1-methylpentanol
b. 2-methyl-2- pentanol d. isopropyl-2-pentanol

30. Which of the following is used to prepare a sulfide

a. c.
from an alkyl halide compound?
a. An alkyl halide in basic condition
b. Sodium hydrosulfide
c. An alkyl halide
d. NaIO4
b. d.
31. What is the description of the compound given?
23. What is the common name of the ether given below?

R R’

a. A Sulfone c. A Sulfide
a. 2-ethoxypropane
b. A Sulfoxide d. A Sulfonoxide
b. 2-propoxy ethane
c. Ethyl isopropyl ether
32. Among the choices given, which would break a
d. Isopropyl ethyl ether
disulfide bond?
a. A strong base with Zn metal catalyst
24. Which of the following is TRUE about ethers?
b. Any strong base
a. Ethers are completely soluble in water.
c. Any strong acid
b. Ethers are reactive towards strong acids.
d. A strong acid with Zn metal catalyst
c. Ethers are not soluble in organic solvents.
d. Ethers form colored complexes with Fe3+
33. Which among the choices is true with the reaction
given?
25. Which of the following compound represents 1,2-
epoxycyclohexane? (1) Hg(OAc)2
(2) NaBH4
a. It undergoes an oxymercuration-demercuration
reaction.
b. It lacks 2-propanol to complete the reaction.
a. c. c. The reagent used to complete the reaction is
H3C wrong. It should undergo hydroboration-oxidation.
d. The reaction cannot happen without a strong acid.

34. Which among the choices is correct?

a. An alkoxymercuration-demercuration undergoes
b. d. substitution reaction.
b. An alkoxymercuration-demercuration undergoes
26. The reaction for the epoxide given started with an elimination reaction.
alkyne forming an alkene. Which among the choices is c. An alkoxymercuration-demercuration undergoes a
the reaction of alkene that would result to the given Markovnikov addition.
epoxide? d. An alkoxymercuration-demercuration undergoes an
anti-Markovnikov addition.

35. Which among the choices is the IUPAC name for the
compound given?
a. Sodium under ammonia solution CH3
b. Hydrogen with a poisonous catalyst
c. Either A or B would result to the same epoxide
CH3CHCH2CH2SH
d. NaNH2 with an alkyl halide
a. 3-methyl-1-butanethiol
27. Which of the following represents the systematic name b. 3-methyl-1-butanesulfide
for the given compound? c. 1-thiol-1,1-dimethylpropane
d. 1-sulfide-1,1-dimethylpropane

36. What is needed to produce sulfone from sulfoxide?

a. NaOH c. NaIO4
a. Butoxypropane c. 1-methylpropylpropane b. HCl d. Hydrogen peroxide
b. 1-methylethoxybutane d. 2-ethoxybutane
37. What is needed to produce sulfoxide from sulfides?
28. Which of the following is the structure for ethyl c. NaOH c. NaIO4
propyl sulfide? d. HCl d. Hydrogen peroxide
SH
38. An alkyne could be reacted to form a ketone using
which of the following reagents?
a. c. a. PCC/CH2Cl2 c. Na2Cr2O7/H2SO4, H2O
b. H2SO4, H2O/HgSO4 d. Wittig reaction

39. Aldehydes and ketones react with hydride reagents to

O form
b. d. None of the choices
a. Alkanes c. Alcohols

Prepared by: Engr. Quennie Marie L. Bañares

 Organic Chemistry 2
b. Alkenes d. Ethers 48. What is the systematic name for the given compound?

40. Carbonyl compounds undergo this type of reaction

a. Electrophilic addition
b. Nucleophilic addition
c. Electrophilic substitution
d. Nucleophilic substitution
a. Methylphenylamine c. N-phenylamine
41. What is the IUPAC name of the compound given below? b. Methylphenylamide d. N-methylamine

49. What would be the product of propanal after

undergoing Clemmensen reduction?
a. Propane c. Propene
a. Ethyl butyrate c. butyl ethanoate
b. Propanoic acid d. Propanone
b. Ethyl butanoate d. butyl ethyl ester
50. Which among the choices is the reactant to complete
42. What is the product when an acyl chloride reacts with
the given reaction?
an alcohol?
a. Ester c. acid anhydride
b. Aldehyde d. carboxylic acid
(1) Na2Cr2O7, H2SO4, H2O
???
43. Which of the following is the expected product for (2) SOCl2
the reaction given?
NH2

+ ???

a. c.

a. c.
N O
b. d.
NH2
b. d.

44. What is the systematic name for the compound given?

a. Ethanoic anhydride
b. 3-carbonyl ester
c. Butanoic ethanoic anhydride
d. Ethanoic propanoic anhydride

45. When acid anhydride reacts with water in pyridine, it

forms which of the following?
a. Acid halides c. Ester
b. No reaction d. Carboxylic acid

46. What is the expected product for the reaction given?

Pyridine
+ HO-CH3 ???

CH3

a.
b. The reagent does not need pyridine; therefore, it
cannot proceed.
c. Both A and D

d.

47. The reaction of a two-carbon alcohol that reacts with

a two-carbon carboxylic acid produces which of the
following?
a. Ethylcarbonyl acid c. Propanoic acid
b. Ethyl acetate d. Propyl acetate

Prepared by: Engr. Quennie Marie L. Bañares