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CPP - SHEET – 1
NOMENCLATURE AND PHYSICAL PROPERITIES
SUBJECTIVE

1. Write the structure and IUPAC name of Glycol and Glycerol.

2. Write the IUPAC name of the following compounds

H H H H NO 2

(a) H3C C C C C CH3 (b)

CH3 OH C2H5 OH OCH3

H3C CH2 C C OH
(c) (d) Benzylic alcohol
CH3 CH2OH

Cl
CH3
(e) H3C
OH

3. Name the factors responsible for the solubility of alcohols in water.

4. Write the IUPAC name of

H3C CH OCH3
(i) m-cresol (ii)
CH3

(iii) Picric acid (iv) [(CH3)3C]3COH

OH

(v) (vi) Isoamyl alcohol

(vii) Catechol (viii) Pyrogallol

CH2OH

(ix) Resorcinol (x)

5. Write the IUPAC name of

(i) Isopentyl phenyl ether (ii) EtO OEt

O
O
(iii) (iv) Br

Br

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Page 2 of 4 CPP - SANKALP_AEP-01-PH-V

CH3 Ph
H3C
(v) (vi)
H O H O

6. Write IUPAC names, as their names by carbinol system, and classify them as 1°, 2°, 3° allylic, vinylic, benzylic
and propargylic of the following compounds.

(i) (ii) Ph OH
OH

(iii) (iv) Et3C—OH

OH

H OH
HO Et
(v) (vi)
H Me

OH OH
(vii) (viii) Ph

OH
OH
Me Me
(ix) Me (x)
Me

7. Write the structure of the following compounds;—

(a) Erythro-3-bromobutan-2-ol (b) 2, 3-Dimethyl cyclo-pentanol
(c) Cyclopentyl-t-butyl ether (d) cis-1, 2-epoxy-4-ethyl cyclohexane

8. Arrange the following compounds in the decreasing order of their boiling points and solubility in water.
(a) i) Methanol ii) Ethanol
iii) Propan-1-ol iv) Butan-1-ol
v) Butan-2-ol vi) Pentan-1-ol
(b) i) Pentanol ii) n-Butane
iii) Pentanal iv) Ethoxyethane
(c) i) Pntane ii) Pentane 1, 2, 3-triol
iii) Butanol
(d) i) Butane ii) Butanol
iii) Pentanol
(e) i) n-Butyl alcohol ii) sec Butyl alcohol
iii) t-butyl alcohol

9. Which of the following is a strongest acid and why?

(a) OH (b)
HO

OH HC
(c) (d)
OH

10. Give the deceasing order of (i) boiling points (ii) solubilities in H2O of the following ethers.
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Page 3 of 4 CPP - SANKALP_AEP-01-PH-V
(a) diethyl ether (C2H5—O—C2H5)

(b) Furan
O

(c) DHF (Dihydrofuran)

O

(d) THF (Tetrahydrofuran)

O

11. Arrange the following

i) H2O, CH3OH, C2H5OH,(CH3)3COH (in acidic strength)
ii) ClCH2CH2OH, CH3CH2OH, NO2CH2CH2OH

12. From each pair, select the stronger base

(a) OH– or CH3O– (each in H2O) (b) CH3CH2O– or CH3CC–
(c) CH3CH2S– or CH3CH2O– (d) CH3CH2O– or NH2–

13. Why an aliphatic alcohol is usually weaker acid than aromatic alcohol?

14. Why an aliphatic alcohol is weaker acid than aliphatic carboxylic acid.

OBJECTIVE

1. Which of the following is a primary alcohol?

(a) Butan-2-ol (b) Butan-1-ol
(c) Propan-2-ol (d) Pentan-2-ol

2. The correct order of boiling point (1°), secondary (2°) and tertiary (3°) alcohols, is
(a) 1°  2°  3° (b) 3°  2°  1°
(c) 2°  1°  3° (d) 2°  3°  1°

3. The decreasing order of acidic character of the compounds CH3C  CH, MeOH, Me2CHOH, Me3COH, H2O is
(a) MeOH  Me2CHOH  Me3COH  H2O  CH3C  CH
(b) CH3C  CH  Me3COH  Me2CHOH  MeOH  H2O
(c) MeOH  H2O  Me2CHOH  Me3COH  CH3C  CH
(d) Me3COH  Me2CHOH  MeOH  H2O  CH3C  CH

4. The decreasing order of acidic character of the following

OH OH C CH COOH

(i) (ii) (iii) (iv)

(a) ii  iv  iii  i (b) i  iii  iv  ii

(c) iv  ii  i  iii (d) iii  i  ii  iv

5. Which of the following alcohol has the highest boiling point

(a) Methanol (b) 2-Butanol
(c) 1-Butanol (d) 2-Methyl-2-propanol

6. Hydrogen bonding is maximum is:

(a) Ethanol (b) Diethyl ether
(c) Ethyl chloride (d) Triethyl amine

7. Which of the following is the most soluble in water?

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Page 4 of 4 CPP - SANKALP_AEP-01-PH-V
(a) iso-Butyl alcohol (b) n-Butyl alcohol
(c) sec-Butyl alcohol (d) tert-Butyl alcohol

8. Which of the following has the highest boiling point?

(a) CH3—O—CH3 (b) CH3—CH2—OH
(c) CH3—CH2—CH3 (d) CH2 = CH—CH3

9. Which is the correct IUPAC name for the following compound?

OH

(a) 4-iso-Propyl-1, 1-dimethyl-1-pentanol (b) 5-iso-Propyl-1, 1-dimethyl-2-hexanol

(c) 1, 1, 4, 5-tetra-Methyl-1-hexanol (d) 2, 5, 6-tri-Methyl-2-heptanol

10. Which of the following would be the least soluble in water?

(a) 1-Propanol (b) 2-Propanol
(c) 1- 5-Pentanediol (d) 1-Hexanol

11. The IUPAC name of ethyl methyl ether is

(a) 1-Methoxyethane (b) Ethoxymethane
(c) 2-Methoxyethane (d) 1-Ethoxymethane

12. Which compound would be the least soluble in water?

(a) CH3—O—CH2—CH2—CH3 (b) CH3—CH2—CH2—CH2—CH3
(c) CH3—CH2—O—CH2—CH3 (d) CH3—CH2—CH2—CH2—OH

——
ANSWER KEY
SUBJECTIVE
11. i) CH3OH  H2O  C2H5OH  (CH3)3COH
ii) NO2CH2CH2OH  ClCH2CH2OH  CH3CH2OH
12. (a) OH– (b) CH3CC–
–
(c) CH3CH2O (d) NH2–
13. Because phenoxide ion is more stable due to resonance.
14. Because aliphatic carboxylic acid is more stable due to equivalent resonating after loosing H+.

OBJECTIVE
1. B
2. A
3. C
4. C
5. D
6. A
7. D
8. B
9. D
10. D
11. A
1-methoxy ethane
12. B
Alkane is almost insoluble in water.
——

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