ChemTech Enrichment Series 2021

Organic Chemistry – Nomenclature.

General Instruction. In a separate answer sheet, shade the letter of the correct answer.

1.

The IUPAC name for is:

A) 6-Ethyl-3,4-dimethylheptane
B) 2-Ethyl-4,5-dimethylheptane
C) 3,4,6-Trimethyloctane
D) 3,5,6-Trimethyloctane
E) 2-(1-Methylpropyl)-4-methylhexane

2.

An IUPAC name for is:

A) 5-Methyl-4-(1-methylpropyl)hexane
B) 2-Methyl-3-(1-methylpropyl)hexane
C) 2-Methyl-3-(2-methylpropyl)hexane
D) 3-Methyl-4-(1-methylethyl)heptane
E) 5-Methyl-4-(1-methylethyl)heptane

3. The correct IUPAC name for the following compound is:

A) 1-Hydroxy-3-sec-butylcyclopentane
B) 3-sec-Butyl-1-cyclopentanol
C) 1-sec-Butyl-3-cyclopentanol
D) 4-sec-Butyl-1-cyclopentanol
E) 3-Isobutyl-1-cyclopentanol

4. What is a correct name for the following compound?

A) 3-Isobutyl-2-methylheptane
B) 3-sec-Butyl-2-methyloctane
C) 5-Isobutyl-6-methylheptane
D) 2-Ethyl-3-isopropyloctane
E) 4-Isopropyl-3-methylnonane
5. What is the correct IUPAC name for the following compound?

A) 3-Hydroxymethylheptane
B) 3-Hydroxymethylhexane
C) 3-Methyloxyheptane
D) 2-Ethyl-1-hexanol
E) 2-Ethyl-1-heptanol

6.

A correct IUPAC name for is:

A) 2-Ethyl-4-pentanol
B) 4-Ethyl-2-pentanol
C) 3-Methyl-5-pentanol
D) 5-Methyl-2-hexanol
E) 4-Methyl-2-hexanol

7. A correct IUPAC name for isobutyl alcohol is:

A) 2-Methyl-1-propanol
B) 2-Methyl-1-butanol
C) 1-Methyl-1-propanol
D) 1,1-Dimethyl-1-ethanol
E) 3-Methyl-1-propanol

8. The correct structure for benzyl alcohol is:

A) I
B) II
C) III
D) IV
E) V
 9.

The correct IUPAC substitutive name for is:

A) 4-Penten-2-methyl-2-ol
B) 4-Methyl-1-penten-2-ol
C) 2-Methyl-4-penten-2-ol
D) 4-Methyl-1-penten-4-ol
E) 4-Hydroxy-4-methyl-1-pentene

10.

The IUPAC name of compound is:

A) 1,1,1-Triethylmethanol
B) 1,1-Diethyl-1-propanol
C) 2-Ethyl-3-pentanol
D) 3-Ethyl-3-pentanol
E) tert-Heptanol

11. The correct IUPAC name for tert-butyl alcohol is:

A) 1-Butanol
B) 2-Methyl-1-propanol
C) 2-Methyl-2-propanol
D) 2-Butanol
E) 1,1-Dimethyl-1-ethanol

12. Which is a correct IUPAC name for CH3OCH2CH2OCH3?

A) 1,4-Dioxane
B) Ethylene glycol dimethyl ether
C) 1,4-Dioxapentalene
D) 1,2-Dimethoxyethane
E) 1,2-Diethoxymethane
13. Select the structure of benzyl methyl ether.

A) I
B) II
C) III
D) IV
E) V

14.

is properly named:
A) cis-1,2-Cyclopentanediol
B) meso-1,2-Cyclopentanediol
C) (1R,2R)-1,2-Cyclopentanediol
D) (1R,2S)-1,2-Cyclopentanediol
E) (1S,2S)-1,2-Cyclopentanediol

15. Which of these is the most accurate name for the molecule

A) sec-Butyl phenyl ether

B) Isobutyl phenyl ether
C) tert-Butyl phenyl ether
D) (R)-2-Phenoxybutane
E) (S)-2-Phenoxybutane

16.

A correct name for is which of the following?

A) (R)-3-Pentyn-2-ol
B) (S)-3-Pentyn-2-ol
C) (R)-2-Pentyn-4-ol
D) (S)-2-Pentyn-4-ol
E) (S)-2-Hydroxy-3-pentyne
17. Which of these, though commonly used, is an incorrect name for (CH3)3COH?
A) tert-Butyl alcohol
B) tert-Butanol
C) 2-Methyl-2-propanol
D) More than one is incorrect.
E) Each is a correct name.

18.

A correct name for the compound, , is:

A) 2-Methyl-4-hexanone D) Ethyl isopropyl ketone
B) 2-Methyl-3-hexanone E) Isobutylpropanone
C) 5-Methyl-3-hexanone

19. What would be a correct name for the compound shown below?

A) tert-Butyl methyl ketone D) Isohexanone

B) 2,2-Dimethyl-4-pentanone E) Isopentyl methyl ketone
C) 4,4-Dimethyl-2-pentanone

20.

A correct name for is?

A) 3-Benzylpropanone D) Nonanone
B) 3-Phenylpropanal E) Nonanal
C) 3-Benzylpropanal

21. A correct name for the following compound would be which of those below?

A) 2,5-Dimethyl-6-hexanal D) 3,5-Dimethylheptanone
B) 2,5-Dimethylhexanal E) 1-Hydro-2,5-dimethyl-1-hexanone
C) 2-Aldehydoisohexane

22.

What is the IUPAC name for ?

A) 4-Oxo-5-phenyl-2-hexanol D) 2-Hydroxypropyl-1-phenylethyl
ketone
B) 5-Hydroxy-2-phenyl-3-hexanone E) 5-Hydroxy-3-keto-2-phenylhexane
C) 2-Hydroxy-5-phenyl-4-hexanone
23. Which is the proper name for the structure shown?

A) 2-Chloro-5-aldehydotoluene D) 4-Chloro-3-methylbenzaldehyde
B) 6-Chloro-3-aldehydotoluene E) 4-Methyl-5-chloro-2-benzaldehyde
C) 2-Methyl-4-aldehydochlorobenzene

24. Which of the following compounds is an acetal?

A) I B) II C) III D) IV E) None of these

25. Which of the following is the best name for the following compound?

A) Propyl isopropanoate D) Ethyl isopropyl ketone

B) Propanoyl isopropoxide E) 1-Methylethyl propionate
C) Isopropyl propanoate

26.

A correct name for is:

A) 2-Methylbutyl 2-methylbutanoate D) Isopentyl isovalerate
B) 2-Methylbutyl 3-methylbutanoate E) Isopentyl isobutyrate
C) 3-Methylbutyl isovalerate

27.

What is the IUPAC name for

A) -Chlorovaleryl chloride D) 1,2-Dichloropentanal
B) 2-Chloropentanoyl chloride E) 1-Chloro-1-butanecarbonyl chloride
C) 1-Chloropentanoyl chloride
 28.

Which is a correct common name for ?

A) Ethylethylisobutylamine D) Ethylethyl-sec-butylamine
B) Diethylisobutylamine E) 2-Diethylaminobutane
C) sec-Butyldiethylamine

29. Which of the following is a tertiary amine?

A) CH3CH2NH2 D) (CH3CH2)4N+ OH-
B) CH3CH2NHCH2CH3 E)

C)

30. A student named a particular compound 2-ethyl-1-butene. Assuming that the student's choice
actually corresponded to the correct distribution of the double bond and the substituents, what is the
correct IUPAC name for this compound?
a. 2-ethyl-1-butene c. 2-methylene-1-pentene
b. 3-ethyl-3-butene d. none of these

31. Cis-trans isomers do not exist for which of the following molecules, all of which have the formula
C3H4Br2?
a. 1,1-dibromopropene c. 1,3-dibromopropene
b. 1,2-dibromopropene d. all of these

32. Cis-trans isomers exist for which of the following molecules, all of which have the formula C 6H12?
a. 2-methyl-1-pentene c. 3-methyl-2-pentene
b. 2-methyl-2-pentene d. all of them

33. Which of the following is a correct IUPAC name?

a. 4-ethyl-1-methylcyclohexene c. 1-methyl-4-ethylcyclohexene
b. 5-ethyl-2-methylcyclohexene d. 5-methyl-2-ethylcyclohexene

34. Which of the following compounds is anisole?

a. b. c. d.

35. Which of the following compounds is an aldehyde?

a. b. c. d.
36. Which of the following compounds is a carboxylic acid?
a. b. c. d.

37. Which of the following is a correct IUPAC name?

a. 2-chloro-3-bromotoluene c. 2-chloro-4-bromotoluene
b. 3-bromo-2-chlorotoluene d. 6-bromo-4-chlorotoluene

38. What is the IUPAC name of ?

a. 2,2-dimethyl-4-butanol c. 1-tert-butyl-2-ethanol
b. 3,3-dimethyl-1-butanol d. 2-sec-butyl-1-ethanol

39. Which of the following is a glycol?

a. HOCH2CH2CH2OH c. HOCH2CH2OH
b. d. none of these is a glycol

40. Which of the following would be the IUPAC name for the ether commonly called ethyl methyl ether?
a. ethoxymethane b. ethoxyethane c. methoxymethane d. methoxyethane

41. Which of the following is the IUPAC name for ?

a. isobutyl mercaptan c. 2-methyl-1-propanthiol
b. sec-butyl mercaptan d. 2-methyl-1-propanethiol

42. Which of the following is a heterocyclic amine?

a. aniline b. benzylamine c. piperidine d. none of these

43. What is the IUPAC name of ?

a. 1-amino-4-methylbenzene c. 4-methylaniline
b. 4-aminotoluene d. p-toluidine

44. What is the IUPAC name of ?

a. 1-amino-4-ethylbenzene c. 1-ethyl-4-aminobenzene
b. 4-ethylaniline d. p-ethyltoluidine

45. What is the IUPAC name of ?

a. ethylaniline c. phenylethylamine
b. ethylphenylamine d. N-ethylaniline
46. What is the IUPAC name of isopropyl amine?
a. propanamine b. 1-propanamine c. 2-propanamine d. 2-propylamine

47. What is the IUPAC name of CH3 NH C2H5?

a. ethylmethylamine c. N-methylethanamine
b. methylethylamine d. propanamine

48. What is the common name of ?

a. methylisopropylamine c. N-methyl-2-propanamine
b. isopropylmethylamine d. none of these

49. What is the IUPAC name of ?

a. methylisopropylamine c. N-methyl-2-propanamine
b. isopropylmethylamine d. none of these

50. What is the IUPAC name of (CH3)2NC2H5?

a. ethyldimethylamine c. N,N-dimethylethanamine
b. dimethylethylamine d. none of these

51. What is the common name of ?

a. ethylpropylmethylamine c. N-ethyl-N-methyl-1-propanamine
b. N-ethyl-N-methylpropanamine d. N-ethyl-N-methyl-2-propanamine

52. What is the name of ?

a. aniline bromine c. anilinium bromine
b. aniline bromide d. anilinium bromide

53. What is the IUPAC name of ?

a. 4-aldyltoluene c. methylbenzaldehyde
b. 4-toluylaldehyde d. 4-methylbenzaldehyde

54. Which of the following is a correct IUPAC name?

a. 1- b. 2- c. 3- d. none of these
methylpropanal methylpropanal methylpropanal

55. How is a compound which contains an aldehyde functionality and a hydroxyl group named?
a. as an aldehyde with a substituent c. as an aldohol
b. as an alcohol with a substituent d. as an alcoal
56. How is a compound which contains an aldehyde functionality and an amine functionality named?
a. as an aldehyde with a substituent c. as an aldamine
b. as an amine with a substituent d. as an aminoal

57. How is a compound which contains an aldehyde functionality and both hydroxyl and amine
functionalities named?
a. as an aldehyde with substituents c. as an amine with substituents
b. as an alcohol with substituents d. such compounds do not exist

58. What is the IUPAC name of HOCH2CH2CHO ?

a. aldopropanol c. 3-hydroxypropanol
b. 2-hydroxypropanol d. 1,3 propanedial

59. How is a compound which contains a ketone functionality and an alcohol functionality named?
a. as an alcohol with a substituent c. as an alkatone
b. as an ketone with a substituent d. as an ketohol

60. What is the IUPAC name of ?

a. 2-hydroxybuatnoic acid c. -hydroxybutanoic acid
b. 3-hydroxybutanoic acid d. -hydroxybutanoic acid