F
|
SOMERS
(Structural & Stereoisomerism)
evel Bed eo alan ae
 
 
 
replace H, with D and H, with H poles
CH ee
HH,
H——Br = ce
ao :
Cty replace Hi with D and H, with H = D
 
 
Relation between (X) and (¥) is:
(a) enantiomers
(©) E and Z isomer
\ (bY diastereomers
(d) constitutional isomer
. Which of the following cyclopentane derivative is optically inactive ? _
H
OH H GY CHy Sen,
@ ® \o =e
H HORGANIC CHEMISTRY for ites
‘pond axis of the compound 9
 
‘Which is the most stable conformer along the 2,3 CC
wc, @,
ff)
)
Hy
   
: ;
H °.
5 eee
arr Hs pees
© 4 /rain edn nin 0 orig 10.
tee
z = E Ncxyon
| @E wz Wee @zz
5 Alegra, « common prescription drug wit the structure shown below, is given fo he
eaten tse ages, How many steogenicebn does Alla Poses”
00H an.
‘ig
4
A
HO"
@1 2 ©3 i @4 12.
6. How many meso isomers of, wll be? ‘
@o @2 2 @3
7. The stable form of trans-1, 4dimethyleyclohexane is represented as:
Hy zo
© LD ®
i CH, 13,
CH;
@ ° Lai,
@
 
irom (Stricture &Stereotomern
‘g. Which fae ane cmt 2
ora (eee) compounds?
HO-CH,-CH,-P
@ oF
‘Which conformer of above compound is mx
(@ staggered iis most table across, ~C.
© gauche () exiped (arity
(@ fal ecieed
reopen ena ue Auorometolone,atercidalant-aflammator agent How many
stereogenic centers does it contain?
ah
Ho Het Yow
He
#
fuorometholone
a
@s 6 7 @s
How many chiral carbons are therein Reserpine (an antipsychotic drug)?
y
o
q
Pp
@s we 7 @s
How many chiral centers are in the following compound ?
6 @7
4 ms
Among the following, the opially inactive compound is:
x ® Le
@ H,cH, C7 é te
HCYou,
© @
Hu)
‘COOH
aS
“ os
#0!
a sone ema ort Gy
seetotte (4) 5 Unknown compound (A) i , mh
Ox ie
(ac) rereomers
(@) Diast
Ht H Boon (© Enantin
0 1H {© Meso compo © tain
oo er 49, Which one of the followings irl
io © {@) 1, 1 Dibromo-1-chloropropane =
fi 1,3 tone.
(© 1, 1Dibromo-3-chloropropane or ire 1
22, Anon folowing he Nes cna, hte
@ 20 oer ons @os
21, The binaphthol (Bmp) is:
 
15. Which of the following compounds might be useful to the chemist trying to
Increase the opis! purty ofthe (@) sample ?
OH
ee
Ho
Hoc
© or
ot
< i
an »
 
16. Which of the following molecules is (are) chiral ?
oo ve
\CH(CHS)2
 
6 o
HC, 4H He, 4H (@) an optically active compound having chiral cet
(b) an optically inactive compound
(© ameso 1d site
(@) an optically active compound witou hang il se
~ ow
(a) and () Mand Iv @ 1,0, Wand VI
© U,WandviWhich ofthe following pais
Br
oa
t
of compounds is pair of enantiomers?
“6D
 
‘The maximum number of stereoisomers thay co
BOB
m6 os @0
“The folowing pair of compounds is best described as:
:
() identical () diastereomers (©) enantiomers
3 the labeled carbons (a and b):
‘Determine the absolute configurations of
 
@a=
 
(@a=R;b=R (Q)a=
following compound in chair form ?
GT
Em A nee @
(seein yoo?
LT Oa=7
o Ey
Which is the most stable chair form of
‘oe
 
 SSRGANTE CHEMISTRY for ee
 
'
at
Cees Lite
ld exist for the compound below ?
@ 16
(@ none of the above
b=R (@a=S;b=S
Which of the structures (a d) willbe produced if a “ting flip” occurs in the. fay
 
H
Ph
Ph
 
ae
op
© 1am
The following compounds diferin respect of
H
Ho’ fA
Ho 7
oe i
{@) their chemical and physial properties
© nothing
(© the direction in which they rotate plane of pla i
(@ thetriverncons wih moles
. Indicate ‘each ofthe following pairs are identical, or?
0 of
Th
ney
 
 
 
 
Br
(@) enantiomers
(©) identical
(© enantiomers
(@ enantiomers
 
diastereomers
‘enantiomers
diastereomers
identical
 
wont oylowing compounds are meso forms ?
Which ofthe felling oo ae as
0H Ha
ts ea
Hon a ae
CH,CH, Cy
1 2 3
(b) 3only.
(@ 2and3
‘34, The separation ofa racemic mixture info pure enantiomers is termed a5 :
(b) Isomerization
@ Equilibration
‘35. Rank of the following groups in order of RS precedence (IV is highest) +
36. Which ofthe following isa meso compound ?
Scuciis  —CH.Dr
2 3
Fe ee
4 gtd 4
re ez ate 4
g
s Hyca g
® bid @
i
Ho "CHCH, HAC’
Pe Al
©™ ero ui,
& ICH,CI
encase CHEMISTRY for ir jeg
ic tamage sn?
(@ amolecule of S-methylheptane
Se
(a) (b)
x
 
 tect isomers am
rows indicate the bonds to be
cts Se Ra
A co eee oe
Ho" 5 \ GH ee
2 BOs cH,
Be ay ® mt oe
giant ©) Lands ee ‘2
ics of the following compounds ga ae
tay ig Compound has a zero dipole moment?
a
 
 
 
 
Sa a
9. onPluto, where everythings rozen, astronauts discovered wo forms of butane gauche and
aie /otog chat ere ne mo roonian
a forms is correct ? und single bonds, which tatement about the
(@ They are enantiomers
(@) They are diastereoisomers
(© They are meso compounds
(@) The gauche form has two stereogenic centers, and the ant has only one
‘40. Which of the following will show optical activity ?
 
cl
c econ Gacy onc
“a CL ®) (© 10H (p) HO H
Ho" Hopton Ho} cri,
@ 50/s0 mixture ofCantp “7 oye z
@ADandE (bd) AandEonly © BCadD —_(@) AlexceptC
41, Among the structure shown below, which has lowest potential energy? fae-76f3]
© Ww @ eo
42, Which of the following molecules is/are chiral ?
ou
By HBr H H "
HB a
9’ Na © oor
cost
»)
ea ie ou @unhi
43. A compound was synthesized by a student, but its structure was not identified.
45.
However, his wonderfully helpful instructor told him that it was a meso
‘compound with 5 carbons and 2 stereogenic centers, Which ofthe following
Structures should te student consider as posibilis for his compour
OH C0,H a a
@ Be noc ton amy
Br
Br
HOF
a) wa
@LnN ony omy nny
How many isomers are possible forthe following molecule ?
;
"(ean coon
Hg6
 
@1 m2 ©3
Which of the following molecules are chiral ?
CH
HO. cH,
o @
Ho" 1H
S H
am, aw
F se &
@10,Wandv  @)t,mandV © Mand (@ Tand 1
46. Which equilibrium is not rapid at room temperature ?
a
wot
a
:
|
 
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a
  
 
 
 
0
ne” Yor,
@ 40m
0s
NO,
@
on
 
   
 
 
 
wo BYoFt
Conn Hoje SO
ON cost CoH
o(P{) OO
H0;6 Ko, No,
$0. Whats the relationship between the molecules in the lowing pis?
0 cao8
x—t-on
x—Lon
Ho—-H ad Ho
HoH
ae
(@) enantiomers _(b) diastereomers (6) idee ay resalesi
[ 30] TORANIE CHEWS re
51, Whatare the correct designations for the structure below ?,
@EE W2E
EZ (@) No geometrical isorners are possible
52, Which ofthe following molecules are chiral ?
1H 9H ae
o se @ AY a mh
ou
 
 
 
 
7 a CH;
ot oO
 
ia ce OY
Fee ee ec
le Cl
(© melting point (@ TUPAC name
Among the following, the most stable isomer is:
eee © Rp one
© peel
Lp ad
56. ‘The most stable conformation of the following compound is
Me
 
oe
 
 
Me
®
Me at
© mi
@ ep,
A Me
TY
Which ofthe folowing moles ke
none a
©) ete ont es i
(Qt anti conformation of1,2-dbromeate
{uD tran, 4bromocyoexae ch 4
tetrabromomethane i, 4 deomocyos
@ (7) 1,1 bromocjeoherane
ah
itt © taay
‘What is the maximum number, @tvaav
imber of stereoisomers possible for dscodermaide?
 
2" 28 om or
‘An aqueous solution containing compounds A and B shows optical activity. A and B are
stereoisomers. Which of the following possibilities eannot be correct?
(@) Anas two chiral centers, but B does so have any because ihasasymmenry plane
(©) A and B are enantiomers
(© A and B are diastereomers
(@ A and B are not present in equal amounts
Which of the following structures represents the lowestenegy form of (1S, 25,
4R) trimethyl -cyclohexane ?
® Ax “Ly
“zy ofA62.
63.
‘Which one of the following isa diastereomer of
(@) (S)-4-bromocis-2-hexene
() (8)-S-bromo-trans-2-hexene
(© (R)-tbromo-rrans-2-hexene
(@ (@)-Sbromo-trans-2-hexene
“The structural formula of cocaine is shown bel
therein this molecule ?
 
Jowr, How many stereogenic carbon atoms are
 
 
 
 
 
 
oy
OCs
@1 @2 Chas @4
Which of the following statements best describes the stereochemical relationships of
‘compound I, ! and Ill shown below ?
Ho. CHO CHO
nt u—-# u——-#
n——cu. CH,
9 HF gp ant is
H——cH, HCH u—j—cH,
u—f—# H—8 H--#
CHO co cho
(@) All compounds are chiral
(b) None of the compounds is chiral
(© Tand I are meso compounds
(@ Tand Ml are diastereomers, and Ills a meso compound,
(©) Land Mare chiral “
‘What is the absolute configuration of the following molecules ? (NS = the molecule has no
‘eenter) Note : For the purpose of this question only, the order of stereocenters is not
o wes y
Bean a @
ay Br
  
ge TereisionsP aE the flowing pana omen
m ov
 
RRS RNs 1
OR RS NS NS One ey
Grenumberofallthepessblestrecionen (8 RS RR
ome ese na
nec: ig
oe
os
2 Ox ae
 
 
 
 
om
o
Dx,
oH be
ox
on
Gon Gon
a =
 
A: Constitutional
1B: Configurational
lc: Conformational
1D: Optical
 
 
 
fa (SJB
 
 
 
 
() I-A-AM-B,V-D
(@ 1-A,-B, I -B,V -D
(@1-8-BU-ANV-B
(© I-B,-A,I-B,IV -D
97. The structural formula of sativene i shown below. How many stereogenic centers are there
inthis molecule ?
w3
@2
@5
4ORGANIC CHEMISTRY for ir,
johexane ?
1s the least stable conformer of I
 
(68. Which ofthe followin
0)
® (Boat)
ae
in-relieving properties, Which
satiomer of bupofen responsible frit pain relieving proper a.
6 The eg rctres sown below i (S)-uprofen?
   
     
 
°
fon yi
x a / py, OH
CA o) Ba
) a You a
y »
°
pts i
 78,
iis tt Sony
 
  
‘A naturally occurring
this constitution ?
 
i Substance has
Ne coin sown below. How many may have
 
 
  
= cic cHeHcircH,
6
 
 
@ 209,36) 200,30)
(© 2), 3¢8)
‘The total number of stereoisomer posi oa
@ 2), 300
le for 2, 3-dichloro butane
 
 
 
 
@2 3 Os fare
Which ofthe following structre isnot meso-2,3-butaneial?
CHy On CH ie
it ‘OH ce CH, He 4 OH. CH,
ern: OH #; © H—}—a, @ HHO
on oa on Gi
 
 
‘A solution of optically active 1 phempethanal racemes in afd aqueous medium. is
jue to
(@) enolization () carbonium ion formation
(© carbanion formation (@ reversible oxidation-reduction
‘The most stable conformation of ethylene glyco is
 
 
 
 
(@) Anti (©) Gauche (© Partially eclipsed (€) Fully ecipaed
Py H
u—t—on wo cx,
Br HL i CH,
Calls ie
‘The molecules represented by the above two arate He
(a) identical es Ean
(©) diastereomers
it = @, —No, @,
The c ler of priority of groups -SCHs ().— NOg. :
Te aa a ts ei
@ Lm, 1,V a TN, a
(© 1,1V, 1,01i CHEWSTRY Free
orca
ration at C-2 and C-3 ofthe compound given:
arm o39
oy
eee
Gis
@ 28,35 25.38
20, Ainonget the faleing mio acs
Gs
om oe
|
NH,
@ mefo#
oot
1. ich of teeing la meso compound?
Gs Gi, — CH H
a ae
(@ Hr © @) Allof these
City HH, (OH
'82. Predict stereochemistry of product when d and Lamine reacts with f-acid:
(@) Diastereomers (b) Meso (© Racemic @ Pure Enantiomer
79. ‘The conf
 
25,38 @ 2R,3R
resented by :
enantiomer is rep
5 Sater eOH
o Mh
City
coon
@ HC NH,
 
 
 
 
 
 
83. How many chiral center (excluding N centres) are there in morphine?
HO,
tH
Ho’
@s4 Or @6 (@ More than 6
‘84. Which dimethyleyclobutane is optically ative ?
(@) eranst,2 ©) aist,2 (© trans-1,3 © cis:,3
85, Which ofthe follwing isthe enantiomer ofthe compound shown below ?
Me ——ar
BH
Me——on
E
 
87
 
90,
a,
 
 
 
ald er Oe o3
0 following compounds ae bes desrtey ©
comers (OT NHOWCH and Sone
(@ enantiomers Koren,
(diastereomers
(0 noe sereoisomess
) conformational isomers (differing by singe :
(0 ona ae gt a at i
‘Cahn-Ingold-Prelog system ‘decreasing priority according to the
TOUGH: “GLB -ci,cite
(@)2>3>1 QS8S> eye 1 {@) No estimate of K can be made
What isthe relationship between the two structures shown ?
ce ae
@) Constitutional isomers
©) Stereoisomers
3 Different leawing of the same conformation ofthese nmpound
ferent conformation ofthe same compound
oe
ae‘Foncanic crevistey
ee
‘92. Which ofthe following tarements is true?
{@) van der Waals’ strain in i, 2-dlmethyigcopm™s
Yan aered stability relative tthe trans isomer
(@) Cyeohexane gives off more heat per CH ouP °°
Feat source of san in the boat conformation of cyclohexane is angle strain
Remmi cin tone oa
seombey (a) Isomer (8) is
coo)
pane isthe principal reason for
1g bummed in ai than any oth,
 
(@ Ph—NO—CH,OH () Ph—CH, —NO2
© Ph—NA—COsH ove
‘94, Which ofthe folowing wil not show geometrical isomerisn
G@ CH, —C = CHC, — Hs © GH, —GI—Gi= CH— CHa — Ci,
ba, Gi,
(@ cH, —CH =H GH, (cH, —CH, — CH =CH— CH, — cH,
The wo compounds shown below are:
 
ae
(@ diastereomers (6) enantiomers (¢) epimers
(96. ‘The molecular formula of diphenylmethane,
©-2O + isCithe
How many structural isomers aré possible when one of the hydrogen is replaced by «
@ regiomers
 
 
chlorine atom ?
@s 4 o8 @7
97. Correct configuration of the following molecule is:
Hs
@ 25,38 () 28,38 © 28,38 @ 2R,3R
98. Maximum enol content isin :
aA °
aX,
ee
 
 
  
300+
101.
102
103.
104
105.
106.
107,
108,
109,
‘which of the following will hay
Giructural & Stercoisomeris
re 7
{@) 2-chlorobutane OMe of the serecisomer mess?
(9 20-tehoopene 2 9ichrbane
‘The correct decreasing order inthe ent cong POPE aid
@irt>0 Ons © om
Total number of stereoisomers of he compos) M2 H>E > m>1
ar donne
‘otal number of stereoisomers of the 13.4?
@o 1 ? iorosrdoherae i
Total number of stereoisomers of the compousy Bescractee
oe ot ou cme
‘Total number of stereoisomers of the com, .
al ee oun 24 eorcepane
In which of the following keto form is more dominating than ena foe
@ o © @ allofihese
‘Among the following compounds which wil give maximum enol content in solution
° ° 9 ° :
i M1 " t
@ CH; —C—CH,—C—CsHls (0) CH, —C—H —C—CHty
° °
IL i
(© CH, —C—CH,—CH,—CH, —(@ GH, —C—cH, —CO0CH,
fe Longecion
©
containing 6g of (+) 2butanal and 4g of
 
 
 
 
f
@ © we © ct
0
Calculate enantiomeric excees of mixture
© -2dutanol.
() 10% 20% (aon
Which ofthe following pair represent ai of datemamess?
(@) Meso tartaric acid and () tartaric acid
@3%
a reili
‘ORGANIC CHEMISTRY fori jee
 
 
oe
a= one
a }—H
) HO——H m4
ae
or} ae Hip - Hy
nt H
ee In
and
ot apo a ee
ea ay
(@ Alof these
110. The stereochemisyof his moledl is:
@ 1R,3R ©) 18,35 © 18,38, @ 15,3R
411. Pure (6)-2-butanol has a specific rotation of +13.52 degrees. A sample of 2-butano!
‘prepared in the lab and purified by distillation has a calculated specific rotation of +6.76
‘degrees. What can you conclude about the composition ?
(2) 50% (S), 50% impurity () 50% (8), 50% (R)
(© 50% (8), 50% racemic (@ some other mixture
112. Determine the absolute configurations of the chiral centres inthe following compound.
   
jb=S —@)a=Rb=R (©) a=S; b-S
   
@a
113.
114.
‘otal numberof stereoisomers possible for following compound is
on = CH—cH,CH,
=ch,
@s ©) 16
a © 32
‘Which is the correct structure of -gyeeraldehyde ? oe
Ho
H
H,0H
for
2 BHO FO. non (@ Alofthese
HoH Gio a
atin Bret 8 Sereobemern
Le e
—CH,— CH, ¢—
16 HOS a? 4
which conformer of above compou
Uonsidr conformer across ce) st sable
@ ag a (b) Gauche ae
b cal, -on © Falepued (Party elie
H OH HO a io
116 HO HHO oops
cHo UP —cH,0n
Tae ee Rs
(0) & @) Configuration of above cabohyirtes, ©
@4 OF lene? pig it)
118, Which ofthe following compound can sow sega tomer <2?
ec co" ucts
a re
+ ® <
F Et ce
@ Semel as om
eC Et cu, Nay
119, Which ofthe following structure represent mes-compound ?
Mey, put ee Lee ot
Me ora, ee
Z aH08
ae wf Tn © 1 ©
Me7 Hi
CoH
1
20, ae
a :
How many fepresentations of lac ai re pase in cher projection (18D?
ay, 28 ow @
Total numberof ster
@s
 
 
 
 
@2
 
4
oslil
4122, The number of stereoisomers formed by the
RGANIE CHEMISTRY fori
i
oo
i wv ‘ch,
A
given compound is
@3
@s
4
428, Which ofthe following compound doesnot undergo Pase- catalyzed exchange
n,0 even though it has an a-hydrogen? *
Og Z 7
i
‘
22, Prodi
he ‘ong time ot
‘densify the product formed inthe above reaction:
2 1D
@ p. ® >
oO iz D
© p. (d) None of these
t
“5
126.
7.
18.
129,
180,
a trical & Stereisomerian lf
‘ig-methyl-2-cyclohexenone =
3 whic
eS wh COS Sts50 "oN ect det
oh
OO
Oy@
ge when it
@ Hills () Hy 1
0 q ats OHH,
o o ro)
‘The tautomer of His:
@t py me (© both Tand I (@) none of these
Ha
4B
Hy
In the enolizaton ofthe given molecule the Hatom involied it
(yeas @) BH © rk (@) cannot be enolized
eS
‘Among the given structure which can exhibit tassomerism ?
Kaisaty (b) only (@ Monty. (@) none of these
,
co Che SS
.
SS
Hen tertiary may tone
ony eth
@ @
ave} ‘ORGANIC CHEMISTRY for I1Tjee
is more sable me.
= she eo utrer hih “0 ne (@ HONE OF these
131. = ee
ay
w
erect aby order of he ven antes eo
ens oboe geneween uate mt @U>U>t
-O-C-
Cuneta ordeal gies econ is
Gifetual& Sterecsomerany
wan CHs.
   
ci
i
H
:0| ov”
product
1e product of this reaction shouldbe
‘The product of this reaction should be
p GH
@ ik as oY
CH
°
io Di (@) Allof these
Sistem @mon>t @U>i>m  @t>m>1 ae
Pease. ‘i : \ \
= x 2s 137. © & QO
133. = [6 6 5 lees oad x
a
336
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Ht
‘Among the given compounds, the correc oder of nl content i
E =—=([ ] @izt>M OW>0>1 Ousisn  @n>m>1
1H
coor Ee eee
eee yey ot Gy ses m3 2>y
OE
o. a
‘Among the given compounds, the correct order of enol contents :
a4, se ON >
 
 
 
 
 
 
 
@tet>m  @iletst @l>iom. ou>m>1
Lee aes IPSC, epresent ena content)
‘ if 19,
Re commrter os: A
Sees Gsryss,  @y>x>z  “e>a>y © ©
‘Among the given compounds, the ext oder of enol contents
Or Ce for Outen mats! Wain @U>t>m
135, ee
©, ay Se aa!
‘Among the given ketone, the one which doesnot enoize
ie i 0c no endl
 
©
(@) none of these
above compound?
How many geometrical isomers are possible fr 98 aa
(9s os‘141. Which ofthe following compound willnot show geometrical fomerism 208
o
 
br Br
@
 
—
eee
Choose the comet relon berween andy?
@b=b hob Ohch
 
143.
Choose the caret relaton berween andy?
hob ~Ohh
@bh (@, andl cannot be compare.
CH, =CH-CH=CH-cH=cH,
How many geometrical isomers are posible fr this compound?
 
oh ws @s es
CH, -CH = ¢-¢ =cH-cH,
if
ow many geometric somes reps fc tino?
(a) 2 4s ws oF @6
CH, -cH Sie:
How many geomerieal anes cihicompunda pose?
@2 03 os «
yon
R R
HO,
ehey
oRGANI CHEMISTRY forte gia Gtractural& Stereoisomerismy
aa 107
cy axsof ormmeny
@dinl G aor these Pe een
a0 oat acive i 0-H Cly oye,
: 5 CH CH 0-Cliy cH, rc Aids
: 7 oS
ce w ye ths Cs
o
18s. sang gcntontin fn) 8 we
@ . "
gap, Which lowing omar center of soy? oss
ee (OBO) acer
ee {@) Structural isomer
© Mena! a owt
7 3
eH : @ | meas Se Se
b