1.

6 1S0MERISM
A.Structural Isomerism
124. How many structural isomers are there of
(a) 3 (b) 4
dimethylcyclopentane
(c) 5
?
(d) 6
125. How many structural isomers are there of
(a) 1 (b) 2
dimethylcyclopropane
(c) 3
?
(d) 4
126. How many structural isomers are there of
(a) 4
dimethylcyclohexane?
(b) 6 (c) 7 (d) 9
127. How many isomeric dibronmobenzenes are possible?
(a) 1 (b) 2 (c) 3 (d) 4
128. Which functional group can be presented in compound having molecular formula C4Ho0
(a) Aldehyde (b) Ketone (c) Acid (d) Alcohol
129. Which functional group is present in compound having molecular formula C4H,0?
(a) Aldehyde (b) Ketone
(c) Unsaturated alcohol (d) Allof these
130. Which functional group is present in compound having molecular formula C4Hg?
(a) Alkane (b) Alkene (c) Alkyne (d) Alcohol
131, Which functional group is present in compound having molecular formula C,Ha0,?
(a) Carboxylic acid (b) Ester (c) Amine (d) Both (a) and (b)
132. How many distinct terminal alkynes with a molecular formula CHo?
(a) 3 (b) 4 (c) 5 (d) 6
133. How many distinct terminal alkenes with a molecular formula C,Hj2?
(a) 3 (b) 4 (c) 5 (d) 6
134. How many distinct terminal alkynes exist with a molecular formula of C
çHg?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
135. How many distinct internal alkynes exist with a molecular formula of C&H,o?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
136. The molecular formula of diphenyl methane is C3 H2
 a
for by
replaced is:
Chemistry
CH00
8(d) (d)
4 5(d) (d)
5 7(d)
is:
is formula (d)
Functional
isomers (d)
Functional
isomers
are:
hydrogen
Organic isomer (b)
Positional
isomers (b) (d)
Functional
isomers
Positional
isomers (b)
Positional
isomers (b)
Positional
isomers
(B)
molecular positional and
(d)
Metamers
Elementary
the ;(A)
?
of
one 7(c) 3(c) (c)
4 (c)
4 6(c) are:
the of -CHCH,
when by number (B)
CO,H
represented for for and are:
possible possible are: (B)
possible compound, (A) (B)
(B) and
; CH,
are are are and ;(A)
metamers (B) ;(A)
isomers
6(b) (b)
2 isomer3
(b) isomer3
(b) given 5(b) CI
144.
CHg
-CH,-CH,-CO,H
OH
OH
structuralether positional positional the (B) (B) (c)
Functional
isomers
For Chain
isomers (a)
Chain
isomers Chain
isomers (a)
Chain
isomers
of ; Metamers (A)
number NO, NO (c)
Metamers (c)
Metamers
many many many
(A) OH OH
How?atom How (a)
2 CH, 4(a) (A)
The1(a)
(a)
4 How (a)
2
(a) (c) CI (A)
(a)
137. 138. 139. 140. 141. 142. 143.
 168. 167. Tautomerism
166.
165. 164. 163.
(a) 1 How (a) 2 162. 161. 160. 159. 158. 157. 20
How (a) Which (a) Functional
isomers
Which isomers
Chain
(c) (a)
CH3
constitutional
(a) What
bromides?
(aalkyl
) 0There (a) How1 (a) How5 (a) 2 (a) 4
many many Number How (a) How4
of -CH,-CHO
of
(A) type are many many many many
tautomers the the
enolizable of
following following ofisomers 8
isomers aldehydesketones structuralall
structural
structural
; (b) 1
(b) 2 are (b) 4 hydrogens (b) that is
will (b) is symmetrical(b) are e
arpossible
possible isomer have (b) 2 (b) 6 (b) 3 isomers isomers
not CH,CH,0CH3 possible isomers (b) 5 (b) 5
formn the
for are of with of of
benzene CH3 molecular of Cg
the there an with Hjmolecular
6
(c) molecular C4H
following enolation?
in (B)
C-CH, and molecular
2
that
(c) 3 the ? formula that
(c) 5 (c) || (c) Metamers CH3CH,CH,OH? have formula
(d)
Positional
isomers(b) (c) (c) 4
following (c) 3formula
(c) 7contain (c) 6 (c) 6
diketone? a
configurational CgHjjformula
; six-member CH,
Relation (d) 3 C;H,0? one
compound? Br.
C4H,0? BrCl?
-bond:
How
between ring
(d) 4 (d) 7 (d) many
(d) (d) (d) 4 (d) 8 (d) 5 (d) 7 ?(d) 7
All
(A) (e) 8 of
conformational
and these
of
these (B) are
is tertiary
:
Organic Chemistry: Some Basic Principles and Techniques
OH
OH
145. ;(A)and (B)are:
(A) (B)
(a) Chain isomers (b) Functionalisomers (c) Metamers (d) Positional isomers
146. O;(0)and (3) are:

(A) (3)
(a) chain isomrs (b) functional isorners
(c) metamers (d) functional isomers
OH
147. OH;(A) and (B) are:
(A) (B)
(a) chain isomers (b) functional isomers
(c) metamers (d) homologues
148. Which of the following pairs represent isomer?
(a) CH -CH3, CH3 CH,-CH,
(b) H,C= CH-OH, CH -0-CHa
(c) CHg -CH,-CH, -CH3, CH3 CH -CH3

CH3
(d) All of these
149. Which of the following represent pair of chain isomers?
(a) n-pentane, Iso-pentane (b) n-pentane, Ne0-pentane
(c) Iso-pentane, Neo-pentane (d) Allof these
150. CH, -CH,-CH,-C==N; CH3 CH-CHz ; (A) and (B) are:
(A)
CN
(B)
(a) Chain isomers (b) Positional isomers
(c) Functional isomers (d) Metamers
151. Molecule of C3Hg with the shortest possible parent carbon chain is :
(a) 5 (b) 6 (c) 7 (d) 8
152. CH -0-CH,-CH,CH3; CH, -CH, -0CH,-CH3
(A) (B)
Relations between (A) and (B) is:
(a) Chain isomer (b) Positional isomer
(c) Functional isomer (d) Metamers
153. How many cyclicstructural isomers are possible for CçHo ?
(a) 4 (b) 5 (c) 6 (d) 7
154. How many structural isomers of CoHa that have a six-membered ring and tri-substituted ?
(a) 5 (b) 6 (c) 7 (d) 8
155. How many structural isomers of C,Hj2 having 3-member ring?
(a) 4 (b) 5 (c) 6 (d) 7
156.How many structural isomer of C6HË2 having 4-member ring ? (d) 6
(a) 3 (b) 4 (c) 5
 20 Elementary Organic Chemistryfor Medical
CH, BrCI?
157. Howmany structural isomers of molecular formula
(a) 4 (b) 5 (c) 6 (d) 7
ring ?
158. How many structural isomers of CaHj6 that have a six-member
(a) 4 (b) 5 (c) 6 (d) 7
159. Number of all structural isomers of CH, that contain one -bond:
(a) 2 (b) 3 (c) 4 (d) 5
160. Howmany kctones is possible with molccular formula CH,,0?
(a) 5 (b) 6 (c) 7 (d) 8
161. How many aldehydes are possible with molecular formula CH0?
(a) l (b) 2 (c) 3 (d) 4
162. There are 8isomers that have the molecular formula CçH,, Br. How many of these are tertiay
alkyl bromides?
(a) 0 (b) 1 (c) 2 (d) 3 (e) 8
163. What type of isomers are CH,CH,0CH3 and CH,CH,CH,OH?
(a) constitutional (b) symmetrical (c) configurational (d) conformational

164. CH3 -CH,-CHO; CH3 C-CH, ; Relation between (A) and (B) is :
(A) (B)
(a) Chain isomers (b) Positional isomers
(c) Functional isomers (d) Metamers
165. Which of the following is isomer of benzene ?

(a) (b) (c) (d) All of these

Tautomerism
166. Which of the following will not form an enolation?

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

167. How many enolizable hydrogens are there in the following compound?

(a) 2 (b) 4 (c) 5 (d) 7

168. How many tautomers are possible for the following diketone?

(a) 1 (b) 2 (c) 3 (d) 4

Organic Ghemistry: Some Basic Principles and Techniques
169. Which of the following will not form an enolate?

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

170. Keto and enol forms of a compound are related to each other as:
(a) resonance structures (b) conformations
(c) configurational isomers (d) constitutional isomers

171. , Enol content of (A) and (B) is:

(A) (B)
(a) B>A (b) A>B (c) A =B (d) A>>> B
172. Which of the following compound will not undergo tautomerism ?
OH

(a) (b) (c) ()

173. Which of the following compound will show tautomerism ?

-C-H
(a) (b) (c) (d) -CH3

174. Which of the following compound has negligible enol ?

(a) =0 (b) (c) (d) CH, CCH, CCH3

KOH
175. (B);Tautomer (B) is:
N

H
(A)
 for Medical
Elementary Organic Chemistry

OH OH
OH
(d)
(c) N
(b
(a) ÓH
H following is :
contents of the
176. Correct order of stability of enol
CH3 -C-CH, -C-0 Et
CH, -C-CH,-C-CH, (c)
CH, -C-CH, (b)
(a) (c) b>c>a (d) a >b>c
(a) a>b>c (b) b>a>c

D,0/DO D,0/DO will give :

177. ; Prolonged treatment of (A) with
(A) D.
D. D D
(b) D (c) (d) D D
D D D D
D
178. How many hydrogens are replaced by deuterium when given compound reacts with D,0 for
long timne

CH -CH,-C-CH ?

(a) 3 (b) 5 (c) 8 (d) 10

D,0/DO
179. CH,-C-CH -CH CH, Which hydrogen will not be replaced by deuterium?
H H, Hg H4
(a) H (b) H; (c) H4 (d) Both (b) and (c)
180.
()
’ (i)
Stability order of enol contents is : ’ (iii)
(a) i> ii > ii
(b) ii >i> ii (c) ii >i> i
181. Which of the following (d) i> iii > ii
compound has highest enol content ?
(a)
(b) ph (C) Ph Ph (d)
 Some Basic Princlples
Organic Chemistry:
forms of 2-butanone ?
following are enol
182, Which of the

CH,CCH,CH,
CH;CHCH = CH,
(a) CH3C = CHCH, and
OH
OH
andCH, CCH,CHg
(b) CH3 CHCH = CH,
OH
OH
CH,=CCH2CH
(c) CH,C CHCH3, CH,CHCH =CH, and
OH
OH OH
= CHCH3
(d) CH,CHCH,CH, and CH,C
OH OH
CCH,CH3
(e) CHC=CHCH, and CH2 =
OH
OH
the most stable enol form of 1,3-cyclohexanedione?
183. Which of the following is

HO OH
HO OH
(b)
(a)
HO
OH HO. (e)
HO (d)
(c)
tautomer ?
compounds has the most stable enol
184. Which of the following
(a) CH,CH (b) CH3CCH3

(d) CHC-CCH3 (e) CH,C-COH

(c) CH,CCH,CCH3 2=0

below are replaced by deuterium when it is shaken in

185. How many hydrogens in the compound
D,O containing trace hydroxide ?

CH, CH,
(c) 3 (d) 6 (e) 7
(a) 1 (b) 2
Organic Chemistry: Some Basic Principles and Techniques
193. Geometrical isomerism result because the molecule:
(a) rotates the plane of polarizcd light
(b) has a plane of symmetry
(c) has acentre of symmetry
(d) has two dissinmilar groups attachcd to both cnds of double bond
194. (i) CH, = CH-CH, CHCH, (i) CH, CH-CH =CH CH,
(ii) CH -CH CH CH=CH-CH
The numbersof possiblegeometric isomers for theabove compounds respectively are:
(a) 0, 2, 4 (b) 2, 2, 4 (c) 0, 3, 3 (d) 0, 2, 3
195. Which of following compound will not show geometrical isomerisrn ?
(a) (b)

(c) (d)
196. Which of the following compound show cis and trans isomerism ?
Br
(a) CICH=CHCI (b) (c) (d)
Br

197. Which of the following compound not show geometrical isomerism ?

CH3
(a) H C c CH, (b) CH3-C=C-CH,
H
CH3 H
(d) Allof these
(c) =C H
198. How many geometrical isomers are possible for given compound ?

(a) 0 (b) 1 (c) 2 (d) 3

199. How many geometrical isomers are possible for ?

(a) 0 (b) 1 (c) 2 (d) 3

200. How many geometrical isomers are possible for given compound ?
C

Cl CI
(a) 0 (b) 1 (c) 2 (d) 3
201. How geometrical
many isomers are possible for :

CH3 CH =C=CH-CH =CH-CH, ?

(a) 0 (b) 1 (c) 2 (d) 3
 Elementary Organic Chemistry for MedicCal
26
forCH,CH=C=C=C= CHCH=CHY.
202. How many geometrical isomers are possible
(b) 2 (c) 3 (d) 4
(a) 1
203. Which of the following compo0Und will not show geometrical isomers ?
C CI DD
(a) (b)

(c) (d) Allof these

C

204. How many geometrical isomers are possible for

(a) 6 (b) 7 (c) 8 (d) 9

205. How many geometrical isomers are possible for ?

(a) 3 (b) 4 (c) 5 (d) 6

206. How many geometrical isomers are CH,
possible for H H
(a) 2 (b) 3
207. How (c) 4 (d) 6
many geometrical isomers
CH, CH=CH-CH =CH-Cl? are possible for
(a) 2
(b) 3 (c) 4
208. How many geometrical (d) 5
isomers
PhCH=CH-CH= (b)CH-Ph?
(a) 2
3
are
possible for
(c) 4
209. How many (d) 5
geometrical isomers are possible for| ?
(a) 0
(b) 1
210. What is the (c) 2
relationship between the following compounds? (d) 3
CH3 H
and
Br
(a) Configurational isomers CH, Br
(c)
Constitutional isomers
211. Which of the (b) Conformational isomers
following can not exist in (d) Structural isomers
diastereomeric pair ?
(a) Cl -Br
(b)
 CH3
CI H C1
(c) (d) H -CI

(b) Optical Isomerism CH,

212. How many stereocentres are there in the following structure?

(a) 1 (b) 2 (c) 3 (d) 4

213. Which of the following diols exists as a pair of enantiomers?
(a) cis-1,3-cyclohexanediol (b) trans-1,3-cyclohexanediol
(c) cis-1,4-cyclohexanediol (d) trans-1,4-cyclohexanediol
214. What is the specific rotation "[J of the following molecule?

= 4.42°
C=0.1g ml!
l= 10cm

(a) + 4.42° (b) +0.442° (c) +44.2° (d) -44.2°

215. If asample of 2-butanol has an enantiomeric excess of 60% of 1-2-butanol, how much of each
isomer is present?
(a) 60% levorotatory and 40% dextrorotatory (b) 80% levorotatory and 20% dextrorotatory
(c) 70% levorotatory and 30% dextrorotatory (d) 66% levorotatory and 34% dextrorotatory
216. How many stereocenters are there in the following molecule?
NH,
HO M

(a) 0 (b) 2 (c) 3 (d) 1

217. Shikimic acid is an important natural product. How many stereoisomers are possible for
shikimic acid?

HÌ
OH

HÌ
OH
(a) 16 (b) 8 (c) 4 (d) 2
218. Explain why the two stereoisomers of 1,4-dimethylcyclohexane are achiral?
(a) Because they are identical
(b) Because they are enantiomers
(c) Because they both have the plane of symmetry
(d) Because there are no stereocenters present in either mnolecule
 Elementary
28 1-ethyl-3-methylcyclohexane?
stereoisomers are there for (d) 6
219. How many (c) 4
(b) 3 different?
(a) 2
following two stereoisomers. How are they
220. Consider the C C1

(a) They have different melting points

opposite directions
(b) They rotate plane-polarized light in
water
(c) They have different solubilities in
refraction
(d) They have different indices of
221. Which of the following compound is chiral ? H

F CH3 F

OH
(a) (b) (c) CHg (d) CIº C Br

H H

222. Identify meso compound:

CH, Cl CI
H C CH, H .C1
(a) (b) (c) (d)
-H
C1
HCHg Cl
CHg Cl

223. In which of the following compound have plane of

CH3 CH,
symmetry ?
Cl Cl
Br
(a) (b) (c) (d) H
CH, CH3 CI
Ci
224. Total number of
stereoisomer
CH, Br H
CH CH
CH CH=CH CH,
CH
(a) 23
(b) 24
CH=C=CH-CH
CH=CH, (c) 25
(d) 26
 Organic Chemistry: Some Basic Principles and Techniques 29

225. ;Relation between (A) and (B) is:

(A) (B)
(a) diastereomers (b) enantiomer
(c) identical (d) structural isomer
CI
226. ;Number of plane of symmetry in above compound is:
CI
Cl
(a) 0 (b) 1 (c) 2 (d) 3
227. Which of the following ischiral compound?

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

-NH,
228. (a) Total number of stereoisomers (a +b=?)
OH

(a) 5 (b) 6 (c) 7 (d) 8

229. Which of the following compound is achiral although it contain chiral center ?
Cl CH3 CH,
H -OH H -OH
(a) BrF (b) (c) (d)
HO H H -OH
CH, CH,
230. Which of the following compound is achiral ?

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

231. CH, --CH, CH= CH-CH-CH, ; Total number of stereoisomers is :

C

(a) 4 (b) 6 (c) 8 (d) 12

232. ’a(stereoisomers) ; ’b (stereoisomers)

a and b are stereoisomers sum of (a+b=?):

(a) 4 (b) 6 (c) 8 (d) 12
 Br
Br
233.
C

sum of siereoisoner(u ) - ?):

(a) 4 (b) 6 (c) 8 (d) 12
234. Which of the following compound is resolvable ?
NO, S0,H NO, SO,H
(a)
(b)
NO, SO,H SO,H NO,
(c) (d)

235. How many planes of symmetry are present in H C r H

H

H
(a) 1 (b) 2 (c) 3 (d) 4
CO,H
HOH
236.
H -OH Number of planes of symmetry in the given compound is:
CO,H
(a) 1 (b) 2 (c) 3 (d) 4
OH
237. (a) (Number of chiral centers)

(b)(Number of chiral centers)

co,H
sum of chiral centers
(a) 3
(a+b=?) is :
(b) 4 (c) 5
238. Which of the following are (d) 6
meso compound ?
H.
CH,OH
Br Br OH

(a) Hy H OH CH¡
(b) HO H (c)
CH, CH, (d) All of these
CH,OH OH
 Organic Chemistry: Some Basic PP
CH, -CO,H
CH-CO,H
stereoisomers are:
HO-CH-CO,H ; Number of chiralcenter and
239. (d) 3, 8
(b) 2, 4 (c) 2, 3
(a) 1,2 as a meso cornpound ?
Which of following compound has one of the stereoisomers
240.

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

H
present in the given compound ?
241. H ;How many plane of symmetry is
Cl
Cl
(c) 2 (d) 3
(a) 0 (b) 1

present in the given compound ?

242. ;How many plane of symmetry is
(c) 3 (d) 4
(a) 1 (b) 2
plane of symmetry and center of symmetry ?
243. Which of the following compound has
F F

F F
F F
(d) All of these
(b) (c)
(a) F F F
F
F
F F
CH3
CH, compound?
244. ; How many chiral center are present in the given

(b) 2 (c) 3 (d) 4

(a) 1
245. How many isomer of CçH,p containing
cyclobutane ring ? (Including stereoisomers)
(b) 6 (c) 7 (d) 8
(a) 5 CH=CH-C!
Cl
246. How many stereoisomers are possible for Cl CH=CH-F

(a) 24 (b) 25 (c) 26 (d) 2?

CH3
247. and ;Number of chiralcenter present in these compougds are :

(a) 0, 1 (b) 0, 2 (c) 9, 3 (d) 1, 2

 Elementary Organic Chemistry for Medical

248. and :Number of chiral center present in these

compounds are:
(a) 1, 2 (b) 2, 2 (c) 2, 1 (d) 2,3

249. -CH3 and ulg Number of chiral center present in these

compounds are:

(a) 1, 1 (b) 1, 2 (c) 2, 2 (d) 2, 1

Et H
250. CH, H and CH,-C-D;Number of chiral center present are:
CH,CH,-CH3
(a) 0, 0 (b) 1, 0 (c) 1, 1 (d) 2, 2
251. Number of stereocentres present in given
compound is :
CH -CH=CH CH-CH
Cl
(a) 2 (b) 3 (c) 4 (d) 5

252. Number of stereocenters present in DI Cl is :

(a) 0 (b) 1 (c) 2 (d) 3

CO,H
H -OH
253. Number of chiral centers present in tartaric acid is:
H+ -OH
CO,H
(a) 1 (b) 2 (c) 3 (d) 4
254. What is the relationship between the following molecules ?
CH,
CH,
H Cl and

H
CH3 CH,CI
(a) Constitutional isomers (b) Enantiomers
(c) Diastereomers (d) Conformational isomers
 33
Organic Chemistry: Some Basic Principles and Technigues
255. What is the relationship between the structures shown below?
CH,Br CH3

H and Br

(a) No isomerism (b) Constitutional isomers

(c) Conformational isomers (d) Configurational isomers
256. What is the relationship between the structures shown below?

H H and H Br

Br Br H Br
(a) Diastereomers (b) Constitutional isomers
(c) Conformational isomners (d) Configurational isomers
257. Which of the following molecule is never chiral?
(a) 2,3-dibromobutane (b) 1,3-dibromobutane
(c) 1,2-dichlorobutane (d) 1,4-dibromobutane
258. Which of the following molecules is chiral?
H H CH3 CH,
CH3 Br CH, -CI
CH3 CI CH, Br
(a) (b) (c) (d)
CH, CH, -CI
CH, CI
CH3
H H CH3 CH,

259. How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?

(b) 1 (c) 2 (d) 3 (e) 4
(a) 0
260. How many asymmetric centers are present in the molecule shown below?
H
CH(CH,) 2
H,C|y

H,C H
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
261. A and B arestereoisomers. They are non-superimposable and are mirror images of each other:.
Which of the following best describes the relationship between A and B?
(a) Structural isSomers (b) Enantiomers
(c) Conformational isomers (d) Diastereomers
34
Elementary Organio Chemistry for Medica
262. What is the e Inionship between the stnuctures shown below?
CI CI

HB and Br -CH,
CH, H
(a) Enantbomers (b) Diastereomers
() Configurational isomers (d) ldentical compounds
263. Which of the following compounds has S configuration?
C
CH,CI CH,CI
(a) (b) (d)
CH,CI C CI CH,CI
264. Which of the following compounds has Rconfiguration?
H
CH = CH,
(a) Br (b) Br H
CH = CH, CH,CH,
(c) Br
CH,CH3 CH,CH,
-CH= CH, (d) CH, = CH
H
Br
265. Which of the following groups has the highest priority using the
Cahn, Ingold, Prelog rules?
(a) -C-OH (b) -C-H (c) -0H (d) -0-CH,
266. WIhich of the following is/are optically inactive?
(a) AS0-50 mixture of R and S enantiomers (b) A
meso compound
(c) Every achiral compound (d) Allof the above
267. If (S)-glyceraldehyde has a specific rotation of -8.7°,
what is the specific rotation of
(R}glyceraldehyde?
(a) -8.79
(b) +8.70
(c) 0.0o
(d) Cannot be determined from the information
given
268. A mixture of equal amounts of two
enantiomers..
(a) is called a racemic mixture
(b) is optically inactive
(c) implies that the enantiomers are meso forms (d) both (a)
and (b)
269. The specific rotation of apure substance is 1.68°. What is
the specific rotation of a mixture
containing 75% of this isomer and 25% of the (-) isomer?
(a) +1.680 (b) 0º (c) +1.26º () +0.84°
Organie Chemistry: Some Basie Principles and Techniques 35

270. (-)Mandelic acid has a specific totation of -158°, What would be the specific rotation of a
soh1tionwhich contains 40% (-)-mandelic acid and 60° (4)-mandelicacid?
(a) +050 (b) +630 (c) +320 (d) -320
271. What is the relationship between the following molecules ?
CH; CH,
Cl4-H H
and
H-CI C H

CH, CH,
(a) Enantiomers (b) Diastereomers
(c) Constitutional isomers (d) Conformational isomers
272. What is the relationship between the following molecules?
CH, CH,
Cl
and
Cl H

CH, CH,
(a) Enantiomers (b) Diastereomers
(c) Constitutional isomers (d) Conformational isomers
273. How many diastereomers exist for the molecule given below?
CO,H
H OH
H -OH
HO

CH,OH
(a) 2 (b) 4 (c) 6 (d) 7
274. Which of the following is a meso compound?
CH, CH, CH, CH,

Hta H -CI
(c)
H Cl
(d)
H C!
(a) (b)
H- Cl Cl H
Ha ClH
CH, CH, CH,CH CH,CH,

275. How many stereoisomers are possible for the following ?

BrCH,CH(CH, )CH,CHg
(a) 0 (b) 1 (c) 2 (d) 4
276. Howmany stereoisomers are possible for the following ?
CH,CHCICH,CHCICH,
(a) 0 (b) 1 (c) 2 () 3
 36
Elementary Organic Chemistryfor Med
277. What is the configuration of the following molecule ?
CH,
H La
Ci

CH,CHs
(a) 2s,3R (b) 3R,3S (c) 2s,3S (a) 2R,3R
278. In the Fischer projecion formula given below, what are the
asymmeuic centers? configurations of the o
CO,H
-CH,
3
H -OH

CH,CH,OH
(a) 2R,3R b) 2R,3S (c) 2S,3R (d) 2s.3S
279. How many chirai carbon centers are present in the
following molecule ?

OH,CH,
CH

(a) 0 (b) 1 (c) 2 (d) 3

280. Which of the following molecule is chiral ?
CHs
Me
(a) (b) NH (C) (d) Boh (a) and(b)
H

C!
281. Which of the following compound has one of the
stereoisomer as a meso compound ?
(a) (b)
(c) 2,3-dimethyl butane (d) Both (a) and (b)
282. Which of the following is diastereomer of
meso-2,3-dichloro butane?
CH3 -C1
CH3 CH,
H
(a) Cl (b) C H
-H H (c) (d) Boç (a) and (b)
H3 H3 H,
 37
Organic Chemistry: Some Basic Principles and Techniques
283. Which of the following has no } 0.S. (plane of symmetry)?
CH3 CH,
(a) (b)
H
ÇH, C1
H
(c) H -CI (d) F -Br

CH3
(2) Conformational Isomerism
284. Which Newmann projection does not represent the following compound?
a
H
Me. Me Me
(a) (b)
H
H H. H
H Me

H
Me H Me

(c) H (d)
Me H
H CI
Me H
285.What are the total number of conformers (staggered and eclipsed) that you can draw for the
following molecule?

(a) 4 (b) 5 (c) 6 (d) 7

286. Choose the correct Newmann projection for 2-methylpentane.
H CH3
H H H
-CH,
(a) H
(b) H
CH, CH,
CH,CH, CH,CH3
H
CH3
H. H H CHg
(c) (d)
H -CH3 H CH,CH3
CH3 H
287. Place the
following
ring reversal. structures properly on the
Elementary Organic Chemistry for Medica.
(abbreviated) energy surface for cyclohexans
4
3

Energy
2 2

a
b= C=
Twist boat d =
Half chair Half chair
Boat
(a) 1=bor c, 2 =a, 3 =d, 4 =b or c
(c) 1=d, 2 =b or c, 3 (b) 1d, 2b or c, 3
=a =d, 4 =a
288. How many eclipsing H-H (d) 1=b or c, 2 =d, 3
=a, 4 =b or c
(a) 1
(b) 2
interactions are there is boat
conformation?(d)
(c) 4
6
289. Identify conformer of
2-methyl pentane:
H
CH3 CH3 CH,
(a)
H H H H CH
(b) Et
H (c) (d)
H
CH, Et H H
CH,CH, CH, H
H
H
OH
H
CH, H

H.
290. , This gauche form is stable when Z is:
H H

H
(a) -F (b) -OH (c) -OCH3 (d) All of these
 Organic Chel

NMC3

291.
. This gauche fon is stable when 2 is:

H
H
(c) -C-OEt (d) -Ph
(a) CH3 (b) Et
ethane are said to differ in:
292. The cclipsed and staggered forms of (c) conformation (d) constitution
(a) molecular formula (b) configuration
following is the staggered conformation for rotation about the C -Cz bond in
293. Which of the
the following structure?
CH3
CH,CHCH,CH,
1 2 3 4

CH3
CH3
CH,CH3 CH,CH,
CH3
(b)
(a)

H CH, H
H H
H
H
H
H CzHs
CH CH3
(d)
(c)
H H H H
H
H

HH

(e)

CH H
H CzHs
energy minimaon agraph of potential energy
294. Among the butane conformers, which occur at
versus dihedral angle?
(a) Gauche only (b) Eclipsed and totally eclipsed
(e) antionly
(c) Gauche and anti (d) Eclipsed only
 contormers
295. Which of the following best explains the reason for the relative stabilities of the
shown?
CH3 CH3
H. H H, CH3

() (II)

H H H H
H
CH,
(a) Ihas more torsional strain. (b) Ihas more steric strain
(c) II has more torsional strain (d) II has more steric strain

WIC REACTION MECHANISM