CHEMISTRY

Class Topic IIT-JEE Achiever BASECamp 2012 - 2013 Solution to Classwork 02 (Main) Basic concepts is organic chemistry Nomenclature, isomerism (including stereoisomers) Polar effects Acidity and basicity, Tautomerism, Reaction intermediates
O C O CH2CH2Cl is

Date: 24-12-2012

1. The IUPAC name of

(A) 1-chloro-2-benzoyloxy ethane (C) 2-chloroethylbenzene carboxylate Ans (C) 2. The IUPAC name of
CH3 is

(B) 2-chloroethylbenzoyl ether (D) 1-phenyl-1-oxo-2-oxychloroethane

(A) 3-cyclobutylcyclopropane (C) 1,3-cyclopropylmethylcyclobutane Ans (B)

O

(B) 1-cyclopropyl-3-methylcyclobutane (D) 2-methylbicyclo [4.3.0] heptane

3. The IUPAC name of HO

OH

is (B) 4-methyl-2-oxo-1,4-butanediol (D) 1,4-dihydroxy-2-pentanone

(A) 3-hydroxybutanoic acid (C) 1,4-dihydroxy-4-methyl-2-butanone Ans (D)

CHOHCH3

4. The IUPAC name of

CH3

is

(A) 1-hydroxyethyl-2-methylbenzene (B) 1-(2 methylphenyl) ethanol (C) 2-(2-methylphenyl) ethanol (D) o-tolylmethylcarbinol Ans (B) 5. Among the following compounds, the strongest base is (A) C6H5NH2 (B) p-NO2C6H4NH2 (C) m-NO2C6H4NH2 (D) C6H5CH2NH2 Ans (D) 6. Give the correct order of decreasing acidity of the following compounds
OH OH OH O 2N CH3 NO2 I NO2 II CH3 NO2 III CH3 NO2 IV OH NO2

(A) IV > I > II > III Ans (A)

2IBC1213CCW-02MS

(B) IV > I > III > II

(C) I > IV >III > II

1

(D) IV > II > I > III

7. Give the correct order of increasing basicity of the following compounds

NH2 OH Me N Me Me Me N Me Me

NO2 II

III

IV

(A) II < I < III < IV (B) IV < III < II < I (C) III < IV < II < I (D) IV < II < III < I Ans (A) 8. Dextrorotatory -pinene has a specific rotation [] 20 D 51.3 . A sample of -pinene containing both the enantiomers was found to have a specific rotation value [] 20 D 30.8. The percentage of the (+) and () enantiomers present in the sample are, respectively. (A) 70% and 30% (B) 80% and 20% (C) 20% and 80% (D) 60% and 40% Ans (D) 9. The total number of stereoisomers of the compound CH3CHBrCHOHCHOHCHBrCH3 is (A) 8 (B) 10 (C) 16 (D) 4 Ans (B) 10. The interchange of two groups (Br and CH3) at the chiral centre of the projection formula (X) yields the formula (Y), while the interchange of another set of two groups (C2H5 and Cl) of (X) yields the projection formula (Z).
CH3 (X) Cl Br C2H5 (Y) Cl Br CH3 C2H5 (Z) C2H5 Cl CH3 Br

Which of the following statements is not correct about the structures (1), (2) and (3)? (A) (Y) and (Z) are identical (B) (X) and (Z) are enantiomers (C) (Y) and (Z) are enantiomers (D) (X) and (Y) are enantiomers Ans (C) 11. The dihedral angle of the most stable conformation of n-butane is (A) 60 (B) 120 (C) 180 (D) 0 Ans (C) 12. The simplest chiral alkane can have the molecular formula (A) C7H14 (B) C6H14 (C) C8H18 (D) C7H16 Ans (D)
CH3 H5 C 2 H C 3 H7

13. Simplest alkene that exhibits only diastereomerism is (A) but-1-ene (B) but-2-ene (C) prop-1-ene Ans (B)

(D) pent-2-ene

2IBC1213CCW-02MS

14. Which of the following are diastereomers?

Ph I H H Br Br COOH II H H COOH Br Br Ph Ph III Br H H Br COOH IV Br H Ph COOH H Br

(A) I and III (B) II and IV (C) II and III (D) all of these Ans (D) The structures I and III do not represent Fischer projection as COOH functional group is not at the top. On rotating I and III by 180, they represented as
Br Br COOH H H Ph I COOH Br H Ph II H Br

On comparing structures I to IV are related as I and II are enantiomers, III and IV are identical or same. The pairs of diastereomers are I and III or IV/ II and III or IV (two pairs of diastereomers) 15. Which of the following free radical is pyramidal?

(A)

(B)

(C) Ans (C)

(D)

. .
or

apocamphoyl radical

Bridgehead free radicals have pyramidal shape because of steric strain, the carbon atom carrying the unpaired electron can not assume a planar geometry. 16. The increasing order of stability of the following carbocations is
+

II

III

IV

(A) I < IV < II < III (B) III < I < IV < II (C) III < IV < I < II (D) II < I < IV < III Ans (C) The carbocation II is aromatic and most stable. Cyclopropylethyl carbocation is more stable than benzyl carbocation. In phenyl carbocation positive charge is on sp2 hybridised carbon hence, least stable

2IBC1213CCW-02MS

17. The order of acidity of following hydrocarbons is

CH3 I II III IV V

(A) III > I > II > IV > V (B) V > II > III > I > IV (C) II > I > III > V > IV (D) II > I > IV > III > V Ans (C) Acidity increases if conjugate base is stabilized by aromaticity resonance/hyperconjugation. Antiaromaticity destabilize conjugate base hence very weak acid. 18. In which of the following hydrocarbons, all carbon-carbon bond lengths are equal. (A) (B) (C) (D)

Ans (D) 19. Consider the following compounds

O I N H II N H O III N H O IV N O

The decreasing order of enolisation of given compounds is (A) III > IV > II > I Ans (D) Higher the stability of enol form, greater be the enolisation. Compound IV does undergo enolisation 20. The reaction intermediate (X) formed in the following reaction is
Br Ph Cl CH3ONa/heat
..

(B) IV > I > III > II

(C) II > IV > II > I

(D) II > III > I > IV

(X)

(A) PhCCl Ans (A)

..

(B) PhCH

(C) PhCBr

..

(D) ClCBr

..

***

2IBC1213CCW-02MS