Organic Chemistry

MCQ

? 1) Which compound would be expected to

(-
>

react more rapidly with a nucleophile ?(2pts)

A. A
A. HCHO B.CH3COCH3
w B
A. B. B
B. A 6.Which of the following compounds can
undergos iodoform reaction ? ( 2 pts)
2)Which of the following shows positive
A.CH3CH2COCH2CH3 B.
conjugative (+C) effect?(1 pts)
CH3CH2CH2CHO
A. -NO2 B. -OCH3 C.-COOH ~ D.-CF3
A. D - C.(CH3)3COH - D.CH3CH2OH
COOH :
A. A
-

B. A
-

-
-
N
I B. D
C. B
C. C
D. C
D. B
3)All of the following saccharides are reducing
7.Which of the following is aromatic ?( 2 pts)
sugars except- (2 pts) CH
B. Maltose 0
CH

A. Ribose C. Sucrose D. 2 2

Fructose Cn
2
cH

A. A
B. B
A. A
C. C
B. B
D. D
C. C
4.Which of the following compounds is the D. D
most basic compound? (2 pts)
A. CH3NH2 0 B. (CH3)2NH C. C6H5NH2 D. NH3 8.Select the one with highest acidity (2 pts)
ali ammoniae WA. Acetic acid B. Methanol C. Phenol D.
E. CH3CH2CONH2 2. aromatic

A. C amide H2O
A. C
B. D
B. B
C. B
C. A
D. E
D. D
E. A
? 9.Answer true or false to the following
5.Which of the following is 5β (beta) series
question:
steroid ( 2 pts)
If a chiral compound is dextrorotatory ,
its enatiomer is levorotatory by the same
number of degrees ( 1 pts) - A. True B.
False
A, B
0 B. A

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 Predict the products for the following reactions

CFzCH,Hz

RICHEUS Alkylation)

CHg = s

CH,CH, CHI CHE

& E
No reaction

-Br
CHCH,C70HCt3

CH3CH, CH,
CHICHe
2
O-C2
CH3CH,
O
CH2
CH2CH3

coxidation too
con

cascrecreateins
CH CHCH(CH3) 2
CH, (H
- =
=

0
nao-coon

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 Chaoxing Questions
MCQ

-
Q1)Which of the following compounds Q5)Rank the following sets of substituents
have a dipole moment of zero? in order of electron-withdrawing inductive
effects.I 2 6 3 -
- -
+

8 j--
(1) -F (2) -Cl (3) -CH3 (4) -Br (5) -I
(6) -H 5
I
8-
~
A. 1 > 2 > 4 > 5 > 6 > 3
~
0 B. 3 > 6 > 5 > 4 > 2 > 1
of ot
C. 1 > 2 > 4 > 5 > 3 > 6
D. 6 > 3 > 5 > 4 > 2 > 1
- ↓-
v Q6)Alkenes and alkynes are unsaturated
hydrocarbons.
~
A. 对
Q2) Rank the following sets of substituents
in order of priority according to the B. 错
sequence rules. C & D
B
(1) -CH2CH3 (2) -CH3 (3) -Br (4) -I Q7)1,2-Dimethylcyclohexene shows cis-
(5) -H⑮ trans isomerism.
v
--
A. 对
A.5 > 2 > 1 > 3 > 4
B.
w 4>3>1>2>5 B. 错
C.5 > 3 > 4 > 2 > 1
D. 1 > 2 > 4 > 3 > 5 Q8)Markovnikov's rule refers to the
regioselectivity of addition
Q3)Rank the following sets of substituents reactions to carbon-carbon double
in order of priority according to the bonds.
sequence rules. ② ③
A. 对
W
(1)⑰-CH3 (2) -COOH (3) -CH2OH B. 错
(4) -OCH2CH=CH2 D

~ Q9)Cyclohexane and 1-hexene are

A.4 > 2 > 3 > 1
constitutional isomers.
B. 1 > 3 > 2 > 4
A. 对
w
C.1 > 2 > 3 > 4
D. 4 > 3 > 2 > 1
↳ Cotiz Gtz
B. 错

Q4)Rank the following sets of substituents Q10)Rank the following sets of

in order of electron-withdrawing inductive substituents in order of electron-
effects. & ⑬ D
withdrawing inductive effects.
(1) -OCH3 (2) -OH (3) -COOH (1) -OCH3 (2) -OH (3) -COOH
(4) -H * (4) -H
oCHI & 3)17274
A. 3 > 4 > 2 > 1
A. 3 > 4 > 2 > 1 or B B. 3 > 4 > 1 > 2
B. 3 > 4 > 1 > 2 not & C. 3 > 1 > 2 > 4
W
bat
v
C. 3 > 1 > 2 > 4 D. 3 > 2 > 1 > 4
H &
D. 3 > 2 > 1 > 4
-

Q11)Compound A (C5H10) does not

dissolve in cold, concentrated H2SO4.
What is A?
25Hio
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H20
 C
d
Q16)Rank the following sets of
~ Ho substituents in order of electron-
-

↓pentere 2-pentene cyclopentane withdrawing inductive effects.

(1) -F (2) -Cl (3) -CH3 (4) -Br (5) -I
->? Q12)What is the major product obtained (6) -H
from the following reaction? A. 1 > 2 > 4 > 5 > 6 > 3
~ 1) 274757673

⑳ B. 3 > 6 > 5 > 4 > 2 > 1

C. 1 > 2 > 4 > 5 > 3 > 6
baseX
sab-> acid
" D. 6 > 3 > 5 > 4 > 2 > 1
I acid

sub- aldehydelketone ketone aldehyde

2
Es
Q17)Which of the following alkene would
you expect to react most rapidly with Br2?
dus
v

Q13)Rank the following sets of

substituents in order of priority according
to the sequence rules. Q18)A tertiary carbocation is more stable
(1) -CH2CH3 (2) -CH3 (3) -Br (4) -I than either a secondary or primary
(5) -H carbocation because ..
4) 3717275

A.5 > 2 > 1 > 3 > 4 A. it carries three positive charges

W
B. 4 > 3 > 1 > 2 > 5 B. it has a pyramidal configuration
C.5 > 3 > 4 > 2 > 1 C.it has a trigonal planar configuration
D. 1 > 2 > 4 > 3 > 5 D.
~ it possesses three electron-donating
substituent groups
Q14)Which of the following isomeric
carbocations is the most stable? Q19)+I effect is shown by
A. -NO2
B. -Cl
C. -Br
-
D. –CH3

⑰ Q15)Which of the following olefins would

you expect to react most rapidly with
concentrated sulphuric acid ?
A.H2C=CH2 HSOL
B. (CH3)2C=CH2
v
C. Cl2C=CCl2
D. CF3CH=CH2

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 plane symmetry (X)
of

Q20)How many chiral centers are there in the 0

Q24)Which compound is ⑧
not a meso
following molecule? compound?
X
v
⑨

B
·
·e ⑤
⑤

⑲
③

⑤ 8

⑤
.......
S

A.7 B. 8 v
C.9 D.10
E.11 A. a
-
B. b
A. A C. c
B. B D. d
C. C
D. D Q25)If a chiral molecule has an absolute
E. E configuration of R, which direction does it
rotate the plane of polarized light?
Q21) Which of the following molecules are a. clockwise (dextrorotatory)
> b. counter clockwise (levorotatory)
chiral? ?
~ -
c. it doesn’t rote the plane of polarized
light

I Wd. can’t be determined from the

information given

A. a
B. b
C. c
Q22)following sets of substituents in order D. d
of priority according to the sequence rules.
Q26)Assign the correct term describing the
(1) -CH3 (2) -COOH (3) -CH2OH relationship to the following two isomers?
(4) -OCH2CH=CH2 4727371
R
~
(a) 4 > 2 > 3 > 1 (c) 1 > 2 > 3 >
4
R
(b) 1 > 3 > 2 > 4 (d) 4 > 3 > 2 >
1
-a.identical
A. a
b.enantiomers
B. b c.diastereomes
C. c d.constitutional
D. d isomers
Q23)How many asymmetric centers does
cholesterol have?
A. 8
~
B. 7
C. 6
D. 5

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Q29)Which molecules have R Q34)
configurations?
A. a
B. b
C. c
D. d

Q30) ~

Q31) Q
3
↳
2345
5)

v ~

v 2

w 2 4

Q32)
↳
2

I
6

Q36)
2

W -
de de a

Q33)
v

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Q37) Q42)
acti (strong (
de

acti(weak)
neutral

de
V

Q38)

de

Q43)

~
I -

Q39) v

-
Q40)

Q44)
lib-dichloro-I-cyclohexene
2 3

allylic

d)b) a) c
~ 0

Q41)
* Q45)
->
4
- bromo hexane
4

ether y
6
·,
0 CH CH
(t
=
-

cr cn -c
e w
= -

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 Q46) Q50)

2:
/
CHCl

Q47)
Q51)
3
substitution Sm7
->

1 ~
2 phenot

Q52)

As 5
B

V is
-

-M3
~

Q50) Q53)
>
vinyl allylic I

04

Q54)
6 5432
4 -hexene-2 of
-

V
w

Q55)
3 2 I

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 converts cyclohexanone into cyclohexane?
(a) NaBH4 (b)
Q56)Which of the following compound H2NNH2 w (c) Zn-Hg,
shows the strongest acidity? HCl (d) H2NOH
A.CH3OH B. CH3CH2OH C.H2O (e) CH3CH2OH
-
D.C6H5OH E.CH3OCH3

Q57)Which of the following compounds Q60)Which of the following

can react with Fehling's reagent? reagents converts
A. C6H5COCH3 B. CH3CH(OH)CH3 benzenecarbaldehyde
B. C. CH3CHO
/ D. (benzaldehyde) into an &
oxime?
CH3CH2COCH2CH3 (a) H2NNHC6H5; (b) H2NNH2;
(c) O3; W
(d) H2NOH; (e) CH3CH(OH)2.
A. A
C. B
D. C Q61)What is the major product of this
E. D reaction?

Q58)Which of the following compounds i

can NOT undergo iodoform reaction? w CH3COCH2COOH +HOOCEHeCOOH
A. C6H5COCH3 v B. CH3CH(OH)CH3
C. CH3CHO w D. Q62)What is the major product obtained
CH3CH2COCH2CH3 A. A from the following reaction?
B. B
C. C
~
D. D w

Q57)Which of the following compounds

can react with hydrogen cyanide?
A. C6H5COOH ~
B. CH3CH2CHO
C. CH3COC6H5 D. Q63)A hydrogen in which position in the
CH3CH2COCH2CH3 A. A structure shown above is most acidic?
B. B
C. C
D. D

Q58)Rank the following compounds from

most reactive to least reactive toward
nucleophilic addition.
(a)CH3CHO (b)C6H5CHO
(c)CH3COCH3 (d)C6H5COCH3 (A) A (B) B (C) C (D) D (E) E
(e)ClCH2CHO A. A
e) a)b)c)d
B. B
A. (a)>(b)>(c)>(d)>(e) C. C
D. D
w
~
B. (e)>(a)>(b)>(c)>(d)

C. (e)>(b)>(a)>(c)>(d)

D. (e)>(b)>(a)>(d)>(c)

E. (a)>(e)>(b)>(c)>(d)
Q59)Which of the following reagents
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Q64) Q68)Select the acid with the highest Ka
(i.e., lowest pKa).

~
w

Q65)Which of the following compounds

can undergo the aldol reaction? Q69)Which one is NOT included in ketone
bodies?
~ ~
a. CH3CH(OH)COOH
b. CH3COCH2COOH
c. CH3COCH3
d. CH3CH(OH)CH2COOH
A. A Q70)Which of the three compounds below
B. B would be the most reactive toward
C. C hydrolysis with aqueous base? acidic ENG4 (stronger).
=>
->

D. D
E. E w

Q66) Which of the following is an acetal?

Q71)Which of the following compounds is

E
methyl propanoate?
~
w

Q67)Which compound would have the

lowest rate of nucleophilic substitution at
its carbonyl group? Q72)What is the major product of this
aromatix + 3EDG
reaction?
w

② ⑭

El
aromatic
Q73)Which of the following compounds
can react with Tollens's reagent?
w

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=> Q74)Which of the following compounds
can NOT undergo decarboxylation?
(00pr/M) B. B. Acetic acid
C. C. Citric acid
v
w D. D. Ascorbic acid
E I
W
B-keto B-hydroxy acid
butanoic butanoic ·hydroxybenzoic
Q81)What is the major product of this
Q75)Which of the following reagents can reaction?
reduce a carboxylic acid into an alcohol?
a. H2/Pt
b. NaBH4
c. Zn-Hg/HCl
v
d. LiAlH4

Q76)Select the one with the highest acidity.

(a) benzenesulfonic acid ⑮55-50gH
O
(b) methanol
(c) phenol Q82)Which of the following compounds
(d) p-nitrophenol can NOT react with Tollens's reagent?
u

(e) acetic acid CH3COOH ~

Q77)What is the major product of this

reaction?

Q83)Which of the following is a d-hydroxy

acid?

Q78)Nitriles are hydrolyzed to.

(a) alcohols Q84)Select the compound with the highest
(b) lactones acidity.
(c) imides A. a
z(d) amides and acids B. b
C. c
D. d
Q79)What is the major product of this
reaction?
Q85)What is the major product of this
reaction?

Q80)The smallest member of carboxylic

acids family is …
y
A. Formic acid
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 *30y
.0xCH3
X v W

Q86)What is the major product of ing -

A. Cellobiose B. Sucrose C. Maltose D.
Lactose v

reaction?
A.A
w
B.B
~ C.C
D.D

I Q91)If two isomers have been classified

Q87)What is the major product of reaction? correctly as epimers , they may also be
I
8 called...?
A. conformers
B. enantiomers
C. diastereomers
~
~ D. tautomers

Q92)Which one of the following

statements is true about the
oxacyclohexane conformer of the sugar b -

-
Q88)Which of the following compounds
can mutarotate?
D-(+)glucopyranose?

(a) One OH group is axial, but all

onthe
glu
remaining substituents are equatorial.
glu (b) The CH 2 OH group is axial, but all I
remaining groups are equatorial.
(c) All groups are axial.
enok
-
~
(d) All groups are equatorial

* Q93)Which of the following represents the

anomer of the compound shown?

Q89)What is the relationship between the

following two carbohydrates? pentose

~
(a) An aldopentose (b) a ketopentose
(c) an aldohexose (d) a ketohexose

E Q95)True or false - Mutarotation is the

establishment of an equilibrium
A. Enantiomers concentration of a and b anomers of a
B. Diastereomers carbohydrate.
A. Yes
C.Epimers
D.Constitutional isomers
v
Q
B. wrong

.
Q90)All of the following disaccharides are
reducing sugars except:
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 OCH3

Q96)True or False - A methyl glycoside of Q103)

a monosaccharide cannot act as a reducing
sugar. A
A. Yes C

B. wrong
L
Q97)True or False - The anomers a - and ~
B b -glucopyranose should form in equal
amounts because they are enantiomers.
A. Yes Q104)
B. wrong

Q98)True or False - The penultimate

- ~
carbon of an acyclic monosaccharide
becomes the anomeric carbon in the cyclic
hemiacetal form of the molecule. Q105)
A. Yes
~
B. wrong
-

Q99)True or False - D-Glucose and D- ~

galactose are diastereomers.
A. Yes ~
/
B. wrong

Q100)
Q106)
3 L I

Q101)

Q107)

-
~

Q102)
1:

2:

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 Q108) Q113)
-

Q114)

Q110)

~ Q115

Q111)

v Q116)

Q112)
-

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Q117) Q120)

Q121)

Q118)

HNO2
I
-

Q122)

43

5 2

Q119)

Q123)

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 Q124)

Q128)

Q125)
Q129)
i ali
(76)a
-
#3
N
-

zali
zal

Q126)

E 54 3

6
a pyrimidine
acid
4-ethyl pyrimidine- 5-carbonylic
Q127)

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SAQ

Q1) Draw the Lewis Structure of CH3Cl, C2H6 , CH2O

Q2) Draw the kekule Structure of CH3Cl . C2H6 , CH2O
Q3) Draw the condensed structures of the following-

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Q4.Draw the skeletal structures of the following

Q5. Write each of the following condensed structural formulas as skeletal structures

p(sp37sp2sp>s
Q6. Rank the following carbon orbitals from lowest to highest in energy - s , p , sp3, sp2 , sp

Q7.Predict the hybridization for each carbon atom in the following moleules –
sp3 sp SP
2
sp

sp2 sp sp2

sp2
sp3
3
sp
sp sp

Q8.Rank in order of increasing bond polarity -

1) N-H, O-H, C-H, H-F C-H<N-H< CH-F
0-4

C-I<C-Br<C-Cl[C- E
2)C-F, C-Br, C-I, C-Cl

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Q9.Circle and name each functional group in the following structures-
alcohol

ketone

benzene
amide
iP
c N2
-

2
ether
Famine amine

Q10.Identify all of the functional groups in the following compounds-

alcohol
amide
amine (2:15:

pyridine
benzene

R ester (R-C-0-R)
Ketone (-C 0)=

alcohol (RHOH) =2'

(R-8"-NH-RL
C

amide
c alkene (RH RH) =

C R

Q11.Arrange each set in order of increasing acid strength.

v ~v
w
1)H2O, NH3, HF, CH4 HF) H20 >NHs7 CH4

HBr> HCR> HE
2)HF, HCl, HBr, HI HI)

H.
3)-C-H, =C-H, ≡C-H =CH) H) C
= -
- C -

Q12.Draw the structures for the nine isomers of C7H16

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 Q13.Give the systematic name for the following compounds :
c
-cH,
6 ↳ 21
2, 2-dimethylbutane

2, 2,4 tumethylhexane 12 50
C-ethyl-5-methylhexane
c -
C

acc -
xc 3,3-diethylhexane
↓ - C

545
c

↳
s-c-c-c-c
cc -
c C
-
as diethyl-octane
4-methyl-
6 7 8

L 5
5-propyl
5-methyl-4-propylheptane 5 7
3 I
4
8 4
4.
4-dimethyl-5-ethyl octane
C- -

C 4- Ciso-propyl) octane
5-tert-butyl. 3-ethyloctane
C
876542 I
8 5 3
4 2

4-ethyl-2,2,7-trimethyloctane CH2C-CHa

Q14.Draw the Newman projection of 1,2-dichloroethane for all staggered and eclipsed conformations , which
has the lowest energy ?Which has the highest energy? anti (180)
Q15.The pharmacophore of dopamine is its most stable conformer , please draw the Newman projection of
that
conformer- Dopamine
H
MHz

"It
Q16.Calculate the degree of unsaturation -
C6H10 , C5H8O, C6H7N
7 1

15 1 2
6 - 6+) -
-

I
+
+ -

61
+ -
34
7 5 2
-
=
6 -
4=
2
=

* Q17. Draw the stable chair conformations of the following compounds-

is"?Icerals H3,1 x rs's

Ins

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