Physical and Chemical Principles Organic Chemistry

REVIEW QUESTIONS AND PROBLEMS

1. Which of the following contains sp-hybridized carbon?
a..C4H8 b. C3H6 c. C5H8 d. C61-112

2. Bond formed in the head-on overlap of two orbitals

a. sigma • b. dative c. pi d. double
3. Part of a molecule where most of its chemical reactions occur
a. single covalent c. triple covalent
b. double covalent d. functional group

4. Which of the following molecules is unsaturated?

a. C3H8 b. CH3OH c. C5Flio d. CH4

5. Name the alkane

a. 2-ethyl-3,4-dimethylpentane c. 3,4,5-trimethylhexane
b. 4-ethyl-2,3-dimethylpentane d. 2,3,4-trimethylhexane
6. Which of the following alkanes is gas at room temperature?
a. octane b. propane c. eicosane d. undecane

7. When ethyl bromide is treated with sodium in dry ether, the product is a.
propane b. butane c. methylpropane d. ethane
8. For the following alkanes, the one with the lowest boiling point

a. 3 b. 2 c. 1 d. can not tell

9. The following reagents will produce an alkane from an alkyl halide except a.
Zn b. Na / dry ether c. alcoholic KOH d. all of these
10. How many possible monochlorinated product is expected from the chlorination of
propane?
a. 1 b. 2 c. 3 d. 4
Physical and Chemical Principles Organic Chemistry

I1. Name the alkene:

a. 2-methyl-2-butene c. 1,2-dimethylpropene
b. 3-methyl-2-butene d. none of the above
12. The name of the saturated hydrocarbon isomer of cis-3-hexene is __________
a. 2-methylpentane c. n-hexane
b. 3-methylpentane d. cyclohexane
13. For which of the compounds below are cis-trans isomers possible?
CH3CH=CH2• CH3CH=CHCH2CH3 CH3CHHCH3
(1) (2) (3)
a. only 2 b. both 1 and 2 c. both 2 and 3 d. all of these
14. When 1-bromo-2-methylcyclobutane is treated with alcoholic KOH, the dominant
product is
CH3
/ C H 3
- 1

a. ______________ b. c. d.
15. Among the following alcohols, methylpropene can be obtained from
a. 1-butanol c. 2-methyl-2-propanol
b. 2-butanol d. all of these
16. Alkenes are commonly prepared via elimination reaction, which of the following is
n_Qt an elimination reaction?
a. Dehydration of alcohol c. Dehalogenation of vicinal dihalide
b. Dehydrohalogenation of alkyl halide d. Hydrogenation of alkynes
17. The following reagents will yield an alkyl halide from an alkene except
a. Br2 / uv or light b. Br2 in CCI4 c. HCI d. HBr / peroxide
18. The acid-catalyzed addition of water to 1-butene will form
a. 1-butanol c. isopropyl alcohol
b. 2-butanol d. propanol
19. The rule which states that; "In the addition of HX to aikenes, the halogen attaches to
the doubly bonded carbon with more alkyl substituent."
a. Saitsev's Rule c. Markovnikoff's Rule
b. Hoffman Rule d. none of these
20. Starting with 2-methy1-2-butene, which of the following processes must be used to
produce a secondary alcol-,c.,1?
a. Acid-catalyzed hydration c. Addition of bromine water
b. Oxymercuration-demercuration d. Hydroboration-oxidation
21. Which of the following reagents will yield a diol from a given alkene?
a. hot, acidic KMnO4 c. 0s04 in NaHSO4
b. 03, Zn and H2O d. H' / H2O

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Physical and Chemical Principles Organic Chemistry

22. Hydrogenation of alkynes in the presence of a poisoned palladium catalyst produces

a. alkane b. alkyne c. alcohol d. alkene
23. Addition of HBr to alkynes results in the formation of
a. geminal dihalide c. tetrahalide
b. vicinal dihalide d. enol
24. When 2-butyne undergoes ozonolysis, the main product is
a. carbon dioxide b. acetic acid c. acetaldehyde d. acetone

25. In hydration of alkynes, the enol formed is found to transform into a ketone. This
form of isomerism is known as ___________
a. geometric isomerism c, keto-enol tautomerism
b. structural isomerism . d. positional isomerism

26. Name the alkyne: H3c 3

a. 4-methyl-2-butyne
c. 2-propynyl-propane
b. 2-methyl-3-butyne d. none of these
27. Which of the following alkynes contain acidic hydrogen?
a. 2-pentyne b. 3-pentyne c. 2-butyne d. propyne
28. Among the folloi.ving molecules, which is not aromatic?

a. c.
d. a l l o f t h e s e

b.

29. All of the following are ortho and para directing substituents except
a.—OH b. — F c. — OR d. — NO2
30. How many isomers does xylene have?
a. 1 b. 2 c. 3 d. 4
31. Vinylbenzene is also known as
c. mesitylene d. durene
a. styrene b. cumene
32. Which of the following carbonyl compounds produce a secondary alcohol with
LiA1H4?
a. aldehyde b. ketone c. ester d. carboxylic acid
33. Addition of methyl magnesium bromide to acetaldehyde produces a.
ethanol b. I -propanol c. methanol d. 2-propanol
34. Oxidation of isopropyl alcohol with KMnO 4 will yield
a. acetone b. acetaldehyde c. acetic acid d. diethyl ether

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Physical and Chemical Principles Organic Chemistry

35. Which of the following alcohols will undergo bimolecular nucleophillic

substitution?
a. 2-methyl-2-propanol c. 2-propanol
b. 1-propanol d. all of these

36. In Williamson synthesis of methyl isopropyl ether, the alcohol used is

a. methanol c. n—propyl alcohol
b. isopropyl alcohol d. ethanol

37. Acid-catalyzed ring opening of an epoxide will result in the formation of a/an
a. monohydric alcohol b. dihydric alcohol c. trihydric alcohol d. enol

38. Which is NOT a physical property of alcohols or phenols?

a. Phenols are generally only slightly soluble in water.
b. The solubilities of normal primary alcohols in water decrease with increasing
molecular weight.
c. The hydroxyl group of an alcohol is non-polar
d. Due to hydrogen bonding, boiling points of alcohols are much higher than those
of corresponding alkanes

39. Hydrocarbon derivatives used as a main ingredient in automobile antifreeze.

a. Ethylene glycol c. Propylene
b. Isopropyl alcohol d. Toluene

40. Which of the following tests will distinguish 1-propanol from 2:propanol?
a. Fehling's Test b. Tollen's Test c. Benedict's Test d. Lucas Test
41. The following reagents will give an alkyl halide from an alcohol except
a. NaCI b. PBr3 c. PC13 d. SOC12
42. Which among the following is a ketone?
a. CH3COCH3 b. (CH3)2CHOH c. CH3OCH2CH3 d. CH 3 CHO
43. Which of the following processes will yield an aldehyde?
a. Oxidation of alcohols using KMnO 4 in basic medium
b. Oxidation of alcohols using chromic acid
c. Ozonolysis of alkene's
d. Ozonolysis of alkynes
44. A tertiary alcohol is produced using Grignard Reagent using a/an
a. ketone b. aldehyde c. alkyl halide d. epoxides
45. Carbonyl compounds can be obtained by reduction using the following except
a. ester b. acyl chloride c: nitrile d. amide

46. Addition of hydrazine to carbonyl compounds produces a/an

a. imine b. oxime c. hydrazone d. semicarbazone
47. Reduction of alkyl phenyl ketones to aromatic hydrocarbons done by Wolf-Kishner
Reduction uses
a. Zn(Hg), HCI b. NH2NH2. KOH c. LiAIH4 d. Fi, with Ni or Pt
48. With the same molecular weight, a carboxylic acid will have a/an _______ boiling
point than an alcohol
a. lower b. equal c. higher d. no basis

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Physical and Chemical Principles Organic Chemistry

49. Acid anhydrides upon hydrolysis yield

a. esters b. amides c. carboxylic acid d. acyl halide
5 0 . H e x a n e d i o i c a c i d i s a l s o k n o w n a s a. malonic acid b. succinic acid
c. glutaric acid d. adipic acid
5 1 . Reaction of alcohol and a carboxylic acid is known as ______
a. saponification b. neutralization c. esterification d. epoxidation

5 2 . Name the acyl halide:

a. butanoyl chloride c. propanoyl chloride
b. chlorobutanoic acid d. none of these

53. Addition of an alcohol to acyl halides produces

a. carboxylic acid c. carboxamide
b. ester d. none of these

54. Name the acidic anhydride:

a. acetic anhydride c. acetic propionic anhydride

b. propanoic anhydride d. none of these
55. Addition of ammonia to acid anhydrides produces
a. carboxylic acid b. ester c. amide d. none of these

0
56. Name the ester:
a. ethyl propanoate c. methyl acetate
b. propyl ethanoate d. ethyl acetate

57. An unknown ester was hydrolyzed with water and acid to produce an acid, X and
alcohol, Y. Oxidation of the alcohol with hot KMnO 4 yielded acid X. Oxidation of
the alcohol produced acetaldehyde. Name the ester.
a. methyl ethanoate c. methyl propanoate
b. ethyl ethanoate d. ethyl benzoate
58. When an ethyl acetate is reduced by LiA1H., the product is _________
a. acetic acid b. ethanol c. acetone d. acetaldehyde

59. Cyclic esters are known as

a. acetals b. diglyme c. lactones d. osazone

60. The scent of a banana is due to the ester

a. ethyl formate b. i-pentyl acetate c. n-octyl acetate d. ethyl butyrate