Organic Chemistry DPP

ORGANIC CHEMISTRY
TARGET DAILY PRACTICE PROBLEMS
IIT-JEE / NEET
DPP
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
I. Write the number of Structural Isomers of given compounds. (Consider only those which is
described in heading.)
Alkenes and cycloalkanes
C3H6 C4H8 C5H10
Alkynes
C3H4 C4H6
Monohalides
C3H7 X C4H9 X C5H11X
Dihalides
C2H4 X2 C3H6 X2 C4H8 X2 C5H10 X2
Alcohols and ethers
C2H6 O C3H8O C4H10 O C5H12 O
Aldehydes and ketones
C3H6 O C4H8 O C5H10 O
Monocarboxylic acids and esters
C2H4 O2 C3H6O2 C4H8 O2 C5H10 O2
Aliphatic amines
C2H7N C3H9N C4H11N
Aromatic compounds
C8H10 C9H12 C7H8O
II. Which of the following compounds show geometrical isomers.

H
CH3 N O
N–H Cl Cl
(1) (2) C=C=C (3)
H H O N
H
(4) CH3–CH=CH–CH=CH–CH=CH–CH3 (5)
(6) Me–CH=C=CH–CH2–CH=C=C=CH–Me (7) (8)
Me
(9) Br – CH = C = C = CH – CH = CH – Br (10) (11)
Me
(12) H3C CH3
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ANSWER KEY
I. Alkenes and cycloalkanes
C3H6 Two (One alkene + one cycloalkane)
C4H8 Six (Four alkene + 2 - cycloalkane)
C5H10 Nine (Five alkenes + 4 - cycloalkanes)
Alkynes
C3H4 Two
C4H6 Six
Monohalides
C3H7 X Two
C4H9 X Four
C5H11X Eight
Dihalides
C2H4 X2 Two
C3H6 X2 Four
C4H8 X2 Nine
C5H10 X2 Twenty one
Alcohols and ethers
C2H6 O Two (One alcohol and one ether)
C3H8O Three (Two alcohols and one ether)
C4H10 O Seven (Four alcohols and three ethers)
C5H12 O Fourteen (Eight alcohols and six ethers)
Aldehydes and ketones
C3H6 O Two (One aldehyde and one ketone)
C4H8 O Three (Two aldehydes and one ketone)
C5H10 O Seven (Four aldehydes and three ketone)
Monocarboxylic acids and esters
C2H4 O2 Two (One acid and one ester)
C3H6O2 Three (One acid and two esters)
C4H8 O2 Six (Two acids and four esters)
C5H10 O2 Thirteen (Four acids and nine esters)
Aliphatic amines
C2H7N Two (One 1°-amine and one 2°-amine)
C3H9N Four (Two 1°-amines, one 2°-amine and one 3°-amine)
C4H11N Eight (Four 1°-amines, three 2°-amines and one 3°-amines)
Aromatic compounds
C8H10 Four
C9H12 Nine
C7H8O Five
II.
Ans. (1), (4), (5), (6), (8), (9) (11)
ORGANIC CHEMISTRY
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DPP
1. ,
Relation between above compounds is :

(A) Position isomers (B) Chain isomers (C) Identical (D) Functional isomers
2. The number of isomeric aldehydes and ketones with formula C5H10O are :
(A) 7 (B) 6 (C) 5 (D) 8
3. CH3CONH2 & HCONHCH3 are called :

(A) Position (B) Chain (C) Tautomers (D) Functional
4. Which is a pair of geometrical isomers ?
(I) (II) (III) (IV)
(A) (I) and (II) (B) (I) and (III) (C) (II) and (IV) (D) (III) and (IV)
5. Cis-trans isomerism is shown by :
(A) (B) (C) (D)
6. The IUPAC name of the compound :
(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

(C) (2Z, 4E, 6Z)-octa-2,4,6-triene (D) (2Z, 4Z, 6Z)-octa-2,4,6-triene
7. S1 : H3C – C  CH has restricted rotation.

S2 : Cyclic compounds have also restricted rotation.
S3 : CH3 – CH3 will show geometrical isomerism due to restricted rotation.
S4 : H3C – C  N has restricted rotation so it shows geometrical isomerism.
(A) T T T T (B) T T F F (C) F F F F (D) T F T F
8. Which of the following compounds will exhibit cis-trans isomerism ?
(A) But-2-ene (B) Propene (C) But-1-ene (D) Benzene
9. The correct stereochemical formula of Trans-3-chloro-1-phenylbut-1-ene is
(A) (B)
(C) (D)
10. The number of geometrical isomers for CH3 – CH = CH – CH = CH – CH = CH2

(A) 2 (B) 4 (C) 6 (D) 8
11. Which of the following compounds will have a zero dipole moment ?
(A) 1,1-dichloroethylene (B) trans-1,2-dichloroethylene
(C) cis-1,2-dichloroethylene (D) none of the above compound
12. (I) (II)
Which of the following physical property is greater for (I) compound.

(A) Boiling point (B) Melting point (C) Solubility (D) Dipole moment
ANSWER KEYS
DPP NO. # 2
1. (C) 2. (A) 3. (D) 4. (C) 5. (A) 6. (C)
7. (B) 8. (A) 9. (D) 10. (B) 11. (B) 12. (B)
ORGANIC CHEMISTRY
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DPP
DPP No. 3
1. The 'E'-isomer is :
(A) (B)
(C) (D) none of the above
2. The 'Z'-isomer is :
(A) (B)
(C) (D)
3. The total number of geometrical isomers possible in following compound is :
(A) 2 (B) 1 (C) 6 (D) 8

4. The number of cis-trans isomer possible for the following compound
(A) 2 (B) 4 (C) 6 (D) 8
5. The number of geometrical isomers of

CH3CH = CH–CH = CH–CH = CHCl is -
(A) 2 (B) 4 (C) 6 (D) 8
6. Which is a pair of geometrical isomers ?

Cl Br Cl Br Cl CH3 H Br
I. C=C II. C=C III. C=C IV. C=C
H Br H CH3 Br H Cl CH3
(A) I and II (B) I and III (C) II and IV (D) III and IV
7. The correct structure of trans-2-hexanal is -

(A) (B)
(C) (D)
8.* Which will show geometrical isomerism ?

Me Me Me Me
(A) CH3CH NOH (B)
Et Me Me Et
H 3C
(C) C NOH (D) HO—N N—OH
H3C
9. Statement-1 : (i) (ii) (i) is more stable than (ii).
Statement-2 : More polar compound is more stable.

(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
(E) Statement-1 and Statement-2 both are False.
Revision Questions
1. Propanone and propanal are :
(A) geometrical isomers (B) chainisomers
(C) functional isomers (D) position isomers.
2.
Relation between above compounds is :

(A) Position isomers (B) Chain isomers (C) Identical (D) Functional isomers
3. Total number of position isomers of dimethyl cyclohexane.

(A) 2 (B) 3 (C) 4 (D) 5
4. The number of isomeric aldehydes and ketones with formula C5H10O are :
(A) 7 (B) 6 (C) 5 (D) 8
5. Mention the correct relationship between (I) and (II)
(A) Chain isomers (B) Position isomers (C) Identical (D) Stereoisomers
Answer Key
DPP No. 3
1. (C) 2. (D) 3. (D) 4. (A) 5. (D) 6. (C) 7. (B)
8.* (ABD) 9. (E)
Revision Questions
1. (C) 2. (A) 3. (C) 4. (A) 5. (B)
ORGANIC CHEMISTRY
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DPP
DPP No. 04
SCQ
Me
CH3 CD2 CH–CH3
C=C CF3
1. 14
CH3 CH2 C=C
H CH2–Cl
Configuration of both the double bond in this compound respectively are
(A) 2E 4E (B) 2E 4Z (C) 2Z 4E (D) 2Z 4Z
2. The number of geometrical isomers in the following compound,
CH3 – CH = CH – CH = CH – C2H5 is -
(A) 4 (B) 3 (C) 2 (D) 5
3. Which of the following statements is not correct ?
(A) Molecules that are superimposable on their mirror images are chiral
(B) Molecules that are not superimposable on their mirror images are chiral
(C) A compound whose molecules are chiral can not exist as diastereomer
(D) A compound whose molecules are achiral can not exist as enantiomers
4. An organic compound with only one carbon will show optical isomerism if –
(A) Four groups attahced to C atom are different
(B) Three groups attached to C atom are different
(C) Two groups attached to C atom are different
(D) All the groups attached to C atom are same
5. The compound having asymmetric carbon atom is –
(A) CH3CHOHCH3 (B) (CH3)2C(C2H5)2
(C) C2H5CHClCH3 (D) C2H5CH (CH3)CH2CH3
6. Which of the following compounds possesses a chiral centre -
H OH
CH3
(A) (B) (C) (D)
MCQ
7. Find out the correct option(s) ?
NH
D
CH3
C=C
(A) C=C Orientation is E (B) H Orientation is Z
H NH
CH3
(C) Orientation is Z (D) geometrical isomers are not possible
CH3
Subjective
8. Arrange the groups or atoms accroding to their priority order using CIP sequence rules ?
(1) , , –CH2–CH3 , –CH=CH2 , –CCH
(2) –COOH, –COCl, –CONH2 ,–CHO, –COCH3
(3) –CH2–NH2, –CH2–Cl, –CH2–Br,–CH2–CN, –CH2–CH2–Cl , –CH2–OH
(4) –CN, –OH, Cl, –D, –H, –SO3H, –SH, –F, Br, I, –NH2
9. Calculate total number of geometrical isomers in following compounds

(i) CH3–CH=CH–CH=CH–CH=CH–CH3
(ii)
(iii) CH2=C=CH–CH2–CH=C=C=CH–Me
(iv)
(v)
(vi) Br – CH = C = C = CH – CH = CH – Br
10. How many chiral carbon atoms are present in the following compounds?
(i) (ii)
(iii) (iv)
MTC
11. Match the following structural formulae with their possible geometrical isomers?
Column I Column II
(Structural formula) (Total geometrical isomers)
(A) CH3–CH = CH CH2–CH3 (p) 8
CH=CH–CH3
(B) CH3–CH = C (q) 6
CH=CH–CH3
(C) CH –CH=CH CH=CH–CH3 (r) 4

3
(D) Cl – CH = CH – CH = CH – CH = CH – CH3 (s) 2
Answer Key
DPP No. 04
1. (A) 2. (A) 3. (A) 4. (A) 5. (C) 6. (A) 7. (ABD)
8. (1) –CCH > > > –CH=CH2 > –CH2–CH3
(2) –COCl > –COOH, > –CONH2 > –COCH3 > –CHO
(3) –CH2–Br > –CH2–Cl > –CH2–OH > –CH2–NH2 > –CH2–CN > –CH2–CH2–Cl
(4) I > Br > Cl > –SO3H > –SH > –F > –OH > –NH2 > –CN > –D > –H
9. (i) 6, (ii) 8, (iii) 2, (iv) geometrical isomerism is not possible, (v) 2, (vi) 4 ]
10. (i) 2, (ii) 3, (iii) 4, (iv) 10 11. (A) – s ; (B) – r ; (C) – q ; (D) – p
ORGANIC CHEMISTRY
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DPP
DPP No. 05
* Marked Questions are having more than one correct option.
1. Indicate the number of chiral carbon atoms in the following molecule.
(A) 6 (B) 7 (C) 8 (D) 9
2.* Which pair is diastereomer :
(A) and (B) and
(C) and (D) and
3.* Which of the following compound will show diastereomerism.
(A) Ph – CC – Me (B) (C6H5)2N2 (C) (D)
4. Statement-1 : and have identical melting points.
Statement-2 : X and Y are identical compounds.

(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(C) Statement-1 is True, Statement-2 is False
5. Match the following compounds with their possible isomerism.
6. Indicate whether each of the following structure has the R configuration or the S-configuration.
(a) (b) (c) (d)
(e) (f) (g) (h)
(i) (j) (k) (l)
(m) (n) (o) (p)
CH2CH3
CH3 H
(q) (r) (s) (t) Br CH3
CH2CH3
(u)
7. Indicate whether each of the following structure has the R configuration or the S-configuration.
(a) (b) (c) (d)
(e) (f) (g) (h)
(i) (j) (k) (l)
(m) (n) (o) (p)
(q) (r) (s) (t)
(u) (v) (w) (x)
(y)
Answer Key
DPP # 05
1. (C) 8 2.* (CD) 3.* (BD) 4. (C) 5. (A) q, (B) s, (C) (p), (D) r
6. (a) R (b) R (c) S (d) S (e) R (f) S (g) R (h) S (i) S (j) S (k) S (l) R
(m) S (n) R (o) S (p) S (q) 2R 3R (r) 2R 3R (s) 2S 3R (t) 3S 4R
(u) 2R 3S
7. (a) R, (b) R, (c) S, (d) S, (e) R, (f) S, (g) R, (h) S, (i) S, (j) S, (k) S, (l) R, (m) S, (n) R, (o) S, (p) S
(q) 2R 3R, (r) 3S 4R, (s) 2S 3R, (t) 3S 4R, (u) 1R 2S, (v) 5R 6S, (w) 3S 4R, (x) 4S 5R,
(y) 2R3R4R
ORGANIC CHEMISTRY
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DPP
DPP No. 06
I. Identify chiral and achiral compounds from the list given below
COOH
CH3 H
H
(1) (2) (3) H H
H CH3
H H
Ph Ph
H3C H
H H
H H
(4) (5) (6) H CH3
COOH COOH
CH O
H3C I Cl
H OH
C C C H OH
(7) (8) (9)
H3C Cl Cl CO2H
C C C C
H H3C CH3
CH3 H
(10) (11) C C (12)
H H
CH3 CH3 NO2 NO 2
H3C Cl
(13) (14) (15)

H3C CH3
CH3 H3C CH3
II. State whether the following statements are True or False.
1. The arrangement in space of the atoms or groups that characterizes a stereoisomer is called its cofiguration.
2. and are enantiomers
3. An achiral molecule always has plane of symmetry as well as centre of symmetry.

4. Molecular symmetry arises only when plane of symmetry & centre of symmetry both are present.
5. Diastereomers are not mirror image of each other.
6. Dextro-isomers rotate the plane of polarized light towards right.
7. Dextro-isomers are represented by putting (D) before their name.
8. Every optically active compound has a racemic form.
9. d-form and -form of an optically active compound have same specific rotation with opposite sign.
10. All forms of compounds containing asymmetric carbon atoms are always optically active.
6. Match the column.
Column I Column II
H COOH
(A) Plane of symmetry (P) H Ph Ph H
COOH H
Ph COOH
(B) Centre of symmetry (Q) H H Ph H
COOH H
H H
C
(C) Show geometrical isomerism (R)
Me COOH
H
C
(D) Show optical isomerism (S) COOH
Me H
Me H
H
C
(T)
H
Me H
Answer key DPP No. 06

1. Chiral : 2, 3, 4, 6, 9, 13, 14, 15 Achiral : 1, 5, 7, 8, 10, 11, 12
II. 1. T 2. T 3. F 4. F 5. T 6. T
7. F 8. T 9. T 10. F 6. (A) Q,T ; (B) P; (C) P,Q,S, T; (D) R,S, T]
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DPP No. 07
1. How many stereoisomers of the following molecule are possible?

HOOC.CH=C=CH.COOH
(A) two optical isomers (B) two geometrical isomers
(C) two optical and two geometrical isomers (D) None
2. CH3 – CH – CH – CH – CH3
| | |
Cl Br OH
Total number of stereoisomers in above compound :

(A) 6 (B) 4 (C) 8 (D) 16
3. Total number of stereoisomer of compound is :
CH3  CH  CH  CH  CH  CH  C 2H5
|
Cl
(A) 2 (B) 4 (C) 6 (D) 8
4. Which of the following pair of isomers can not be separated by fractional crystallisation or fractional distillation:
(A) Maleic acid and Fumaric acid
(B) (+)-Tartaric acid and meso - tartaric acid
(C) CH3  CH  COOH and H2N  CH2  CH2  COOH

|
NH2
(D) (+)-lactic acid and (–)-lactic acid
5. The enantiomeric excess and observed specific rotation of a mixture containing 6 gm of (+)-2-butanol and 4
(gm) of (–)-2-butanol are respectively (If the specific rotation of enantiomerically pure (+)-2-butanol is + 13.5
unit).
(A) 80%, + 2.7 unit (B) 20%, – 27 unit (C) 20%, + 2.7 unit (D) 80%, – 27unit
6*. Which of the following statements is/are not correct for D-(+) glyceraldehyde?
(A) The symbol D indicates the dextrorotatory nature of the compound
(B) The sign (+) indicates the dextrorotatory nature of the compound
(C) The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer projection diagram
(D) The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer projection
diagram
7.* Which of the following will show optical isomerism as well as geometrical isomerism.
(A) (B) (C) (D)
8*. Which of the following compounds are optically active?

(A) CH3.CHOH.CH2.CH3 (B) H2C=CH.CH2.CH=CH2
HOOC NO2
(C) (D)
NO2 COOH
9*. Which of the following pairs can be resolved?
(A) (B)
(C) (D)
10. The simplest alkane which can exhibit enantiomerism has -

(A) 5 carbon atoms (B) 6 carbon atoms (C) 7 carbon atoms (D) 4 carbon atoms
Answer key
DPP No. 07
1. (A) 2. (C) 3. (D) 4. (D) 5. (C) 6*. (AD) 7.* (ACD)
8*. (ACD) 9*. (BCD) 10. (C)
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DPP No. 08
1. Which of the following can exist as diastereomers -

(A) Lactic acid (B) 1-Butene (C) 2-Butene (D) Ethane
2. (+)-Tartaric acid and meso-tartaric acid are -

(A) Enantiomers (B) Diastereomers (C) geometric isomers (D) None of these
3.* Which pair is diastereomer :
(A) and (B) and
(C) and (D) and
4.* Which of the following compound will show diastereomerism.
(A) Ph – CC – Me (B) (C6H5)2N2 (C) (D)
5.* Which of the following statements are correct ?

(A) Molecules that are superimposable on their mirror images are chiral
(B) Molecules that are not superimposable on their mirror images are chiral
(C) A compound whose molecules are chiral can not exist as diastereomer
(D) A compound whose molecules are achiral can not exist as enantiomers
Comprehension
S(+) Mono Sodium Glutamate (MSG) is a flavour enhancer used in many foods. Fast foods often contain
substantial amount of MSG and is widely used in Chinese food. If one mole of above MSG was placed in
845 ml solution and passed through 200 mm tube, the observed rotation was found to be + 9.6°.
+
COO¯Na
¯OOC—CH2—CH2—C

NH3 H
MSG
6. Find out the specific rotation of (–) MSG:
(A) + 24° (B) + 56.8° (C) – 48° (D) None of these
7. Find out the approximate percentage composition of (–) MSG in a mixture containing (+) MSG and
(–) MSG whose specific optical rotation is –20°.
(A) 83.3 % (B) 16.7 % (C) 91.6 % (D) 74 %
8. If 33.8 g of (+) MSG was put in 338 ml solution and was mixed with 16.9 g of (–) MSG put in 169 ml solution
and the final solution was passed through 400 mm tube. Find out observed rotation of the final solution
(A) + 1.6° (B) + 4.8° (C) + 3.2° (D) None of these
9. Statement-1 : and have identical melting points.
Statement-2 : X and Y are identical compounds.

(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
10. Match the following compounds with their possible isomerism.
Answer Key (DPP No. 08)
1. (C) 2. (B) 3.* (CD) 4.* (BD) 5.* (BCD) 6. (D)
7. (C) 8. (C) 9. (C) 10. (A) q, (B) s, (C) (p), (D) r
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DPP No. 09
1. Which of the following will not show optical isomerism.
(A) Cl–CH=C=C=CH–Cl (B) Cl–CH=C=C=C=CH–Cl
H
Cl H
COOH
H OH
(C) (D)
H OH
Me Cl
COOH Me
2. The structures shown here are related as being :
Br
H Br
H3C C
CH3 C H
H3C
CH3 C H
C
Br H
Br
(I) (II)
(A) conformers (B) enantiomers

(C) geometrical isomers (D) diastereoisomers
3. W hich of the Newman projections shown below represents the conformation about the C 1–C 2
bond of 1 Bromo –2–methylpropane?
(A) (B) (C) (D)
4. Which of the following sawhorse representation is correct for the given newman projection.
(A) (B)
(C) (D)
5. Which point on the potential energy diagram is represented by Newman projection shown here ?
(A) P (B) Q (C) R (D) S
6. Which of the following is correct P.E. diagram for propane ?
(A) (B) (C) (D)
7. Which statement is correct about anti conformation of 1-Chloropropane ?

(A) It is the most polar form (B) It has maximum torsional strain
(C) It has minimum steric strain (D) A and C both
8. The most stable conformation of 3-fluorobutan-2-ol is :

(A) Fully eclipsed form (B) Partially eclipsed form
(C) Gauche form (D) Anti form .
9.* What is correct about (B) & (C) ?

CH3
D H
–180° +180°
(C) rear (B)
front
carbon carbon
H D
CH3
(A) Both are achiral molecules (B) Both contains chiral carbon
(C) Both are meso (D) Both having same bond length.
10. Which of the Newman projections shown below represents the most stable conformation about the C1–C2
bond of 1-iodo-2-methyl propane?
(A) (B) (C) (D)
11.* Which of the following conformers of 1,2-diol cannot form intramolecular H-bond ?
OH OH OH OH
OH
H OH H H HO H
(A) (B) (C) H (D)

H H H H H H
H HH
H OH H
12. Which is the lowest energy conformation of butane?

CH3 CH3
H CH3
(A) (B)
H H H H
H3C H H H
CH3 CH3
H H H3C H
(C) H H (D) H H
CH3 H
13. Study carefully the conformational structure of following compound given below and predict out the compound
with the name given in option A and B.
H
H3C CH3 CH3 H3C H H
H H
CH3 CH3 CH3
C C C C
(a) H3C (b) H (c) C 2H 5
(d) H3C
H H3C
H 5C 2 H3C H H CH3
CH3
CH3 CH3
H H CH3 H3C C 2H5
H H H
H CH3
(e) (f) C 2H 5 (g) (h) CH3
H CH3 H3C C 2H 5
H3C CH3 H CH3
CH3 CH3
A. 2-methylbutane Answer Box :
B. 2,3-dimethypentane Answer Box :

14. Examine the following formulas and select those pairs that satisfy the following conditions :
C2H5
H CH3 H3C H CH3
H3C
CH3 H
(a) (b) (c)
CH3 H
C2 H5 H H CH3
H H3C
CH3
C2H5
H H
H CH3
C2H5
(d) C C (e)
H3C
CH3 H H3C H
CH3
(A) Which are identical in all respects ? Answer Box :
(B) Which are conformational isomers ? Answer Box :
(C) Which are constitutional isomers ? Answer Box :
ANSWER KEY
DPP NO. # 9
1. (A) 2. (D) 3. (C) 4. (D) 5. (B) 6. (A) 7. (D)
8. (C) 9.* (A,B,C,D) 10. (C) 11.* (B,C) 12. (C)
13. A - b, d, e; B - a, c, f, h;
14. (A) c & e, b & d, ; (B) a & b or a & d; (C) a & c or a & e, b & c, b & e, c & d
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP No. 10
1. Which of the following orders is not correct regarding the –I effect of the substituents ?
(A) – I < – Br < – Cl < – F (B)
(C) (D)
2. Write resonating structure for each of the following :
(a) ( b) ( c)
(d) ( e) (f) – CH = CH2

O
|| ..
(a) CH3  CH  CH  C  CH3 (b) H 2 N CH  CH  C  N (c)
 ..
(d) CH3 – O – CH = CH – (e) (f) CH3  C  O :
(g) (h) (i)
(j) (k) (l) CH2 = C = O (m)
ANSWER KEY
DPP NO. # 10
1. (C)
2. ( a) (b)
( c)  
(d) 
( e)  (f)  – CH = CH2
3. (a)
(b) (c)
(d)
(e)
(f) (g)
(h)
(i)
(j)
+ + ..  
..
(k) (l) CH 2 = C = O C H2 – C  O
+
–2 
(m) N– N  N
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP No. 11
1. Which of the following statements is (are) true about resonance.

(a) Resonance is an intramolecular process.
(b) Resonance involves delocalization of both  and  electrons.
(c) Resonance involves delocalization of  electrons only.
(d) Resonance decreases potential energy of a molecule.
(e) Resonance has no effect on the potential energy of a molecule.
(f) Resonance is the only way to increase molecular stability.
(g) Resonance is not the only way to increase molecular stability.
(h) Any resonating molecule is always more stable than any nonresonating molecule.
(i) The canonical structure explains all features of a molecule.
(j) The resonance hybrid explains all features of a molecule.
(k) Resonating structures are real and resonance hybrid is imaginary.
(l) Resonance hybrid is real and resonating structures are imaginary.
(m) Resonance hybrid is always more stable than all canonical structures.
2. Following are the canonical structure of naphthalene :

1 1 1
2 2 2
3  3  3
4 4 4
Which of the following statements is true about the C1–C2 and C2–C3 bond lengths :
(A) Both bonds are of same bond length.
(B) C1–C2 bond is longer than C2–C3 bond.
(C) C1–C2 bond is shorter than C2–C3 bond.
(D) It is not possible to judge the bond lengths because given structures are tautomers.
3. In which of the following molecules –electron–density in ring is maximum :
NO2 O NH 2 OCH3
(A) (B) (C) (D)
 
4. CH2=CH–OCH3 C H 2  CH  O CH 3
(I)
 
CH2=CH–NHCH3 C H 2  CH  N H CH 3
(II)
Which of the following statements is true about the contribution of I & II in respective resonance hybrids:
(A) Both I and II have same contributions.
(B) I contributes more than II.
(C) I contributes less than II.
(D) It is not possible to judge their relative contributions.
I
2
NO2 3 NO2
1
5. 4 6
5
NO2
Which of the following statements is true about this molecule :

(A) C5–N bond is longer than C1–N and C3–N bonds.
(B) C5–N bond is shorter than C1–N bond and latter is shorter than C3–N bonds.
(C) All three C–N bonds are of same length.
(D) C1–N and C3–N bonds are of same length but they are longer than C5–N bond.
ANSWER KEY
DPP No. 11
1. (a), (d), (g), (j), (l), (m) 2. (C) 3. (B) 4. (C) 5. (D)
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP No. 12
(a) (b) (c)
(d) (e) (f ) – CH = CH2

O
|| ..
(a) CH3  CH  CH  C  CH3 (b) H 2 N CH  CH  C  N
(c) (d) CH3 – O – CH = CH –
 ..
(e) (f) CH3  C  O :
(g) (h)
(i) (j)
(k) (l) CH2 = C = O (m)
2
1 3
3.
4
Which of the following statements is true about this molecule.

(A) C1–C2 and C3–C4 bonds are of same length.
(B) C1–C2 bond is shorter than C3–C4 bonds.
(C) C1–C2 bond is longer than C3–C4 bond.
(D) C1–C2 and C2–C3 bonds are of same length.
4. Which of the following compounds do not have all C—O bonds of same length :
(A) CO2 (B) HCOOH (C) CO32– (D) HCOO–
5. Which of the following compounds do not have all C—C bonds of same length :
(A) (B) (C)  (D) 
6. Resonance effect is not observed in :

O

OH Cl N NH3
(A) (B) (C) (D)
O
7. Pairs of structure which are resonance structure.

OH O
||
(A) CH = C - H + CH  C  H
2 2
• •
(B) CH2=CH–CH=CH2 C H 2  CH  CH  C H 2
(C) CH2=CH–OH CH 3  C  O
|
H
NH 2 NH 2
| | 
(D) CH 3  CH 2  C  NH 2 CH 3  CH 2  C  N H 2

8. Identify the major contribution in following resonance structures :

NH 2 NH 2
| | 
(A) NH 2  C — N H 2 NH 2  C  N H 2

O O O O
||  || || |
(B) CH 3  C  C H  C  CH 3 CH 3  C  CH  C  CH 3
O
–
O
(C)

O O
| •• |
(D) CH 3  C  O H CH 3  C  O  H
 •• 
ANSWER KEY
DPP No. 12
1. (a) (b)
(c)  
(d) 
(e)  (f )  – CH = CH2
O
||
2. (a) CH3  CH  CH  C  CH3 (a)
..
(b) H 2 N CH  CH  C  N (b)
(c) (c)
(d) CH3 – O – CH = CH – (d)
(e) (e)
 ..
(f) CH3  C  O : (f)
(g) (g) (h)
(h)
(i) (i)
(j) (j)
+ +
(k) (k) (l) CH2 = C = O
+
..   –2 
..
(l) CH 2 = C = O C H2 – C  O (m) (m) N– N  N
3. (B) 4. (B) 5. (B) 6. (D) 7. (D)

8. (A) II (B) II (C) I (D) II
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
Write the stability order with reason.
S.No. Resonating structures Order of stability Reason
- +
(1) H2C CH Cl H2C CH Cl
(a) (b)
-
O O
(2)
(a) (b)
- -
(3) CH2 CH NH H2C CH NH
(a) (b)
+ +
(4) CH3 O CH2 H3C O CH2
(a) (b)
+
- - +
(5) H N C O H N C O H N C O
(a) (b) (c)
Me N Me +
N -
O O O O
(6)
(a) (b)
H +
O OH
(7)
(a) (b)
O O OH
(8)
(a) (b) (c)
(9)
(a) (b) (c)
-
O O
-
(10) O O
(a) (b)
-
S S
(11)
H H
(a) (b)
+ -
(12) H O C N H O C N
(a) (b)
-
O O O
(13)
C
(a) (b) - (c)
N N N
-
O O O
(14)
C C C
(a) (b) - (c)
N N N
- -
O O O
(15) - -
H CH2 H CH2 H CH2
(a) (b) (c)
+
O O
(16)
(a) (b)
-
N N N
(17)
(a) (b) (c)

- -
O O O O O O
(18)
(a) (b) (c)
N
-
(19) N
(a) (b)
-
O O O
(20)
(a) (b) (c)
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP NO. # 23
1. Which of the following is the correct stability order for given carbocations ?


(1) (2) (3) (4)



(5)
(A) 5 > 4 > 2 > 1 > 3 (B) 3 > 4 > 2 > 1 > 5
(C) 3 > 5 > 2 > 1 > 4 (D) 1 > 3 > 5 > 4 > 2
2.  rearranged carbocation is -
(A) (B) (C) (D)
Ag 
3.  Rearranged Carbocation + AgBr
Rearranged carbocation is :
(A) (B) (C) (D)
4. The –ve charge (anion) which is not delocalized by resonance in given species.
(i) (ii) (iii) (iv)
(v) (vi) (vii) CH3 – C  C– are
(A) (i) only (B) (i), (iv), (v), (vi), (vii) only
(C) (i), (v), (vi), (vii) only (D) all
5.* Select the correct order(s) :
(A) > .......... (Stability)
(B) > .......... (Acidic-strength)
(C) > .......... (Acid-strength)
(D) < .......... (Acid-strength)
reaction
6.   Rearranged most stable Carbocation is
(A) (B) (C) (D)
7.* Which of the following carbocations would you expect to rearrange.
(A) (B)
 
(C) Ph — CH2 — C H — CH3 (D) CH3 — C — CH — CH3
| |
CH3 OCH3
8. Statement 1 : When an isobutyl carbocation is generated in D 2O / D3O  , tert-butyl alcohol is formed

containing no deuterium attached to carbon atom
Statement 2 : In 1,2-hydride shift during rearrangement of carbocation the following mechanism is possible.
(D) Statement-1 is False, Statement-2 is True
9. Match the carbocation (I) with the rearranged carbocation (II).
10. Match the properties of column II with the pair given in column I.
Column – I Column – II

(A) NH2 < N2 (p) leaving group ability in SN reaction
(B) F < I (q) Nucleophilicity
(C) < (r) basicity
(D) > (s) Stability
ANSWER KEY
DPP NO. # 23
1. (A) 2. (B) 3. (B) 4. (C) 5.* (ABD) 6. (C)
7.* (CD) 8. (C) 9. (A – s) ; (B – r) ; (C – q) ; (D – p).
10. (A – p,s) ; (B – p,q,s) ; (C – q,r) ; (D – p,s).
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP NO. # 24
1. Racemic mixture is obtain in which substrate when it is treated with CH3OH
(A) (B) (C) (D)
2. Which of them is correct order for solvolysis rate in aqueous acetone
CH3O–CH=CH–CH2–Cl P
Ph–CH2–Cl Q
CH3O–CH2–CH=CH–Cl R
CH3O–CH2–CH2–CH2–Cl S
(A) R > P > Q > S (B) P > Q > R > S (C) Q > P > S > R (D) P > Q > S > R
3.
P1 and P2 are respectively :
(A) , Br CH2Br (B) , Br

Br
Br Br
(C) , (D) ,
Br Br
NaOH / H O
2
4.* 
Which of the following statements are correct about the above reaction
(A) The reaction is SN1 reaction
(B) The reaction intermediate is carbocation
(C) The major product will be (d+l) mixture of 2,3-dimethylpentane-3-ol
(D) The major product has one stereogenic centre
A/R
5. Statement-1 : 3-chlorocyclopropene is solvolyzed in methanol at much higher rate than 5-chlorocyclo
penta-1, 3-diene.
Statement-2 : The intermediate carbocation of 5-chlorocyclopenta-1,3-diene is more stable than the
carbocation formed by 3-chlorocyclopropene.
6. Statement 1 : A bridge head halide like norboryl bromide is inert for SN1 reaction
Statement 2 : Carbonium ion at bridgehead position cannot be formed because planarity is not possible.
Subjective
7. Write the correct decreasing order of solvolysis of these halides ?
(a) (I) (II) (III) (IV) (V)
(b) (c)
(d) (e)
ANSWER KEY :
DPP NO. # 24
1. (C) 2. (D) 3. (C) 4.* (ABCD) 5. (C)
6. (A) 7. (a) II > III > I > V > IV ; (b) II > I > III ; (c) III > I > II ; (d) III > I > II (e) II > III > I
ORGANIC CHEMISTRY
IIT-JEE / NEET
DPP
DPP NO. # 25
H O / Acetone
1. 2    Possible no. of product and fractions on fractional distillation are respectivily..
(A) 2, 1 (B) 4, 2 (C) 6, 3 (D) 8, 4
2. The poduct in the given reaction is
+ P
(A) (B)
(C) (D)

Et O (1eq)
3. + CH3CH2CI   
EtOH
major product is :
(A) (B) CH3 – CH2 – OCH3
(C) CH3 – CH2 – O – CH2CH3 (D)
4. X+Y (where Y = hydrocarbon)
In the above reaction which of the following statement is correct.
(A) Step-1-is an SN2 reaction
(B) The hydrocarbon product of step-1 is CH3(CH2)2CH3
(C) X = cyclopentadiene
(D) the nucleophile in 2nd reaction is
5. STATEMENT-1 :- Rate of solvolysis of (II) is faster than (I).
Cl
–– ––
Cl
–– ––
H3C – C – CH3
H3C – C – CH3
––
––
CH3
(I) (II)
STATEMENT-2:- The carbocation intermediate of (II) formed in solvolysis reaction is stabilized by resonance
and hyperconjugation.
6. Which is correctly method :

Reactant Product Type of reaction
(A) + PhSH + NaOH PhSMe SN1
(B) + CH3OH SN2
(C) + HCl SN2
(D) + aqueous AgNO3 SN1
7. Mark the T for true or F for false statements respectively about the following reaction
KI131
  Product
DMSO
S1: The rate of each of these reactions depended on both [R–I] and [131I – ]
S2: Loss of optical activity was exactly twice as fast as gain of radioactivity.
S3: Each molecule undergoing substitution suffers Inversion of configuration
S4: The reaction mixture will have optical rotation zero in equilibrium
(A) T T T T (B) T T F F (C) T F T F (D) T T T F
Write Up
Effect of substrate structure on SN2 reactivity :
Branching at the  and -carbons decreases the rate of SN2 reaction due to increase in steric crowding
around the reaction site.
Unsaturation at the -carbon i.e. in allylic or benzylic systems rate of SN2 reaction increases probably owing
to resonance stabilisation in transition state.
unsaturation at -carbon i.e. vinylic, acetylenic and aryl substrate are very unreactive towards SN2 reaction
or it is stopped altogether.
O
||
With -substitution (compounds of formula ZCH2–X when Z = RO–, RS–, R – C – etc.) rate of SN2 increases
due to increase in electron deficiency at reaction site increasing rate of attack of nucleophice.
8. For each pair of compounds state which compound is the better SN2 substrate.
(a) and
(I) (II)
(b) and
(I) (II)
(c) and CH3 — CH2 — CH2 — Br
(I) (II)
(d) and
(I) (II)
(A) a – II, b – I, c – I, d – II (B) a – I, b – II, c – I, d – II
(C) a – I, b – II, c – II, d – I (D) a – I, b – II, c – I, d – I
9. In which reaction methyl iodide is formed with fastest rate
H 
(A)  (B) 


(C)  H
(D) CH3–OH 

Subjective
10. For each of the following solvolysis reaction give the products (major as well as minor)
(a) CH OH 
3 (b) aq.ethanol
  

(c) (d) aq. AgNO

3

 
11. How many of the following compounds will give white precipitate with aqueous AgNO3.
Cl Cl Cl
Cl O
Cl Cl
Ph Ph
| | Cl
Ph — C — C — Ph
| |
OH Cl
ANSWER KEY
DPP NO. # 25
1. (B) 2. (A) 3. (A) 4. (B) 5. (D) 6. (D) 7. (A)
8. (D) 9. (B)
3CH OH , 
 
10. (a) S N 1 alcoholysi s +
aq .ethanol
(b)  
 +
SN1
(c) +
aq . AgNO
3
   
  +
SN1
11. 4

Organic Chemistry DPP

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Organic Chemistry DPP

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ORGANIC CHEMISTRY

TARGET DAILY PRACTICE PROBLEMS

II. Which of the following compounds show geometrical isomers.

(4) CH3–CH=CH–CH=CH–CH=CH–CH3 (5)

(6) Me–CH=C=CH–CH2–CH=C=C=CH–Me (7) (8)

(12) H3C CH3

Relation between above compounds is :

3. CH3CONH2 & HCONHCH3 are called :

4. Which is a pair of geometrical isomers ?

(I) (II) (III) (IV)

5. Cis-trans isomerism is shown by :

(A) (B) (C) (D)

6. The IUPAC name of the compound :

(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

7. S1 : H3C – C  CH has restricted rotation.

9. The correct stereochemical formula of Trans-3-chloro-1-phenylbut-1-ene is

10. The number of geometrical isomers for CH3 – CH = CH – CH = CH – CH = CH2

12. (I) (II)

Which of the following physical property is greater for (I) compound.

1. (C) 2. (A) 3. (D) 4. (C) 5. (A) 6. (C)

7. (B) 8. (A) 9. (D) 10. (B) 11. (B) 12. (B)

(C) (D) none of the above

3. The total number of geometrical isomers possible in following compound is :

(A) 2 (B) 1 (C) 6 (D) 8

(A) 2 (B) 4 (C) 6 (D) 8

5. The number of geometrical isomers of

6. Which is a pair of geometrical isomers ?

7. The correct structure of trans-2-hexanal is -

8.* Which will show geometrical isomerism ?

(A) CH3CH NOH (B)

Statement-2 : More polar compound is more stable.

Relation between above compounds is :

3. Total number of position isomers of dimethyl cyclohexane.

5. Mention the correct relationship between (I) and (II)

(1) , , –CH2–CH3 , –CH=CH2 , –CCH

(2) –COOH, –COCl, –CONH2 ,–CHO, –COCH3

(3) –CH2–NH2, –CH2–Cl, –CH2–Br,–CH2–CN, –CH2–CH2–Cl , –CH2–OH

9. Calculate total number of geometrical isomers in following compounds

(A) CH3–CH = CH CH2–CH3 (p) 8

(C) CH –CH=CH CH=CH–CH3 (r) 4

(D) Cl – CH = CH – CH = CH – CH = CH – CH3 (s) 2

1. (A) 2. (A) 3. (A) 4. (A) 5. (C) 6. (A) 7. (ABD)

8. (1) –CCH > > > –CH=CH2 > –CH2–CH3

(A) 6 (B) 7 (C) 8 (D) 9

2.* Which pair is diastereomer :

(A) and (B) and

(C) and (D) and

3.* Which of the following compound will show diastereomerism.

(A) Ph – CC – Me (B) (C6H5)2N2 (C) (D)

4. Statement-1 : and have identical melting points.

Statement-2 : X and Y are identical compounds.

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

(e) (f) (g) (h)

(i) (j) (k) (l)

(m) (n) (o) (p)

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

(e) (f) (g) (h)

(i) (j) (k) (l)

(m) (n) (o) (p)

(q) (r) (s) (t)

(u) (v) (w) (x)

(13) (14) (15)

2. and are enantiomers

3. An achiral molecule always has plane of symmetry as well as centre of symmetry.

1. (A) 2. (C) 3. (D) 4. (D) 5. (C) 6. (AD) 7. (ACD)

8. (ACD) 9. (BCD) 10. (C)