EXCEL 2022

GENERAL ORGANIC CHEMISTRY

MIXED GOC, ACID & BASES, DIPOLE 03J

Marking Scheme : Single Correct (+3,-1) M M: 51 Time : 30 min

1. What is the pKa of Ethane?

(a) 4.5 (b) 50 (c) 15.7 (d) 15
2. Estimate the pKa of the proton indicated
H

(a) 50 (b) 35 (c) 25 (d) 5

3. Which of the following reactions does not occur as shown:
(a) CH3CC–Na+ + CH3CO2H  CH3CO2–Na+ + CH3CCH
(b) CH3CC–Na+ + CH3OH  CH3O–Na+ + CH3CCH
(c) CH3CCH + NaNH2  NH3 + CH3CC–Na+
(d) CH3CCH + NaOH  H2O + CH3CC–Na+
4. Of compounds (i) and (ii), ___ is the stronger acid and of compounds (iii) and (iv), ___ is the stronger
base

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

N
H
(a) (i) and (iii) (b) (i) and (iv) (c) (ii) and (iii) (d) (ii) and (iv)
5. Which is the following compounds is most acidic:
OH OH OH
(a) Cl CH 2 CH 2 OH (b) (c) (d)
NO2
6. Which of the following compounds will react with sodium hydroxide solution in water?
(a) C6H5OH (b) C6H5CH2OH (c) (CH3)3COH (d) C2H5OH
7. Correct order of acidic strength of given compounds will be?

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

(a) (iv) > (ii) > (i) > (iii) (b) (iv) > (iii) > (i) > (ii) (c) (iv) > (i) > (ii) > (iii) (d) (iv) > (i) > (iii) > (ii)
8. Which compound would be most acidic?
(a) CH3CH2CH3 (b) CH3CH=CH2 (c) Cyclohexane (d) CH3(CO)CH3 (e) Benzene

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9. Chose the order that has the following compounds with respect to decreasing acidity.
O OH
OH OH C

(i) (ii) (iii)

(a) (ii) > (iii) > (i) (b) (ii) > (i) > (iii) (c) (i) > (ii) > (iii) (d) (i) > (iii) > (ii) (e) (iii) > (i) > (ii)
10. Which base is strong enough to convert (CH3)3COH into (CH3)3CONa in a reaction that goes to comple-
tion?
(a) NaNH2 (b) CH3CH2Na (c) NaOH (d) CH3COONa (e) More than one of the above
11. Among the following compounds, the one that undergoes deprotonation most readily in the presence of
base, to form carbonion is-
O O O O O O O
(a) (b) (c) (d)
MeO MeO H
12. Which hydrocarbon in the following molecule would you expect to be the most acidic (i.e., most easily
removed as H+)?

(a) (b) (c) (d)

13. Based upon a understanding of product stability, predict the product formed when the following dianion
reacts with one equivalent of acid.
O O OH O O OH O O O O O O
H (a) (b) (c) (d) (e)

14. Rank the following in order of relative acidity (more acidic going to less acidic)
O
OH
(p) COOH (q) (r) H 2SO4 (s) OH
F
(a) q > r > p > s (b) r > p > s > q (c) s > r > p > q (d) r > s > p > q (e) q > p > s > r
15. Arrange the following compounds in order of decreasing acidity.
OH OH OH OH

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

Cl
(a) (ii) > (i) > (iv) > (iii) (b) (i) > (ii) > (iii) > (iv) (c) (i) > (ii) > (iv) > (iii) (d) (ii) > (i) > (iii) > (iv)
16. Most acidic phenol derivative is:
OH OH OH OH

(a) (b) (c) (d)

17. Among the following compounds, the most acidic is:

(a) p-nitrophenol (b) p-hydroxybenzoic acid (c) o-hydroxybenzoic acid (d) p-toluic acid

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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