Professional Documents
Culture Documents
Biomolecules
Solutions
SECTION - A
Objective Type Questions (One option is correct)
50 C
H /H O
1. X + NH3 Y 2 H2N – CH2COOH Compound X is
(1) Chloroacetic acid (2) Bromoacetic acid (3) Both (1) & (2) (4) Acetic acid
Sol. Answer (3)
NH
X — CH2COOH
3
H2N — CH2 — CO O N H4 NH2 — CH2COOH
Hydrolyses
(x) 50C
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266 Biomolecules Solutions of Assignment (Set-2)
It is due to isomerisation that fructose reduces Tollen’s reagent although it does not contain an–CHO group
5. D-glucose reacts with phenylhydrazine to make osazone. How many molecules of phenylhydrazine are used
for this reaction per molecule of D-glucose?
(1) One (2) Two (3) Three (4) Four
Sol. Answer (3)
CHO CH = N.NHC6H5 CH = NNHC6H5
C6H5NH NH2 C6H5NHNH2
CHOH CHOH C=O
–H2O
(CHOH) 3 (CHOH)3 (CHOH) 3
C = N. NHC6H5
CH (OH) 4
CH2 OH
(Osazone)
6. In alkaline solution D-glucose, D-mannose and D-fructose are in equilibrium. This reaction is known as
(1) Fries rearrangement
(2) Lobry de Bruyn-van Enkelstein rearrangement
(3) Hofmann rearrangement
(4) Kolbe's reaction
Sol. Answer (2)
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Solutions of Assignment (Set-2) Biomolecules 267
7. During mutarotation of -D-glucose in aqueous solution angle of optical rotation
(1) Remains constant value of + 111°
(2) Remains constant value of + 19.2°
(3) Changes from an angle of +112° to a constant value of +52.5°
(4) Changes from an angle of +19.2° to a constant value of +52.5°
Sol. Answer (4)
CH2OH CH2OH
O O
H H O
H H
O O
OH H OH H
H H
H OH H OH
R R R
| H
+
+ |
–
OH
– |
–
H3N — CH — COOH H3N — CH — COO H2 N — CH — COO
(at lower pH) (at higher pH)
Zwittor ion
(moves towards cathode) (moves towards anode)
10. If a native protein is subjected to physical or chemical treatment which may disrupt its higher structure without
affecting primary structure then this process is called
(1) Inversion of protein (2) Denaturation of protein (3) Renaturation of protein (4) Fermentation
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268 Biomolecules Solutions of Assignment (Set-2)
11. Ring structure of glucose is due to formation of hemiacetal and ring formation between
(1) C1 and C5 (2) C1 and C4 (3) C1 and C3 (4) C2 and C4
Sol. Answer (1)
H H CH2OH
C—
——O C—
OH
—
6
| | O
H — C — OH H — C — OH 5
H H
| | H
HO — C — H HO — C — H 4 1
| | OH H
O OH OH
H — C — OH H — C — OH 3 2
| |
H—C—OH H— C H OH
|
CH2OH CH2OH
HCl
C12H22O11 H2O C6H12O6 C6H12O6
D glu cos e D fructose
[ ]D 66.5 [ ]D 52.5 [ ]D 92.4
Hydrolysis of sucrose to an equimolar mixture of D (+) glucose and D (–) fructose is accompanied by a
change in the sign of optical rotation from dextro rotatory to laevorotatory , the overall process is called inversion
of sugar
13. Which of the following gives an optically inactive aldaric acid on oxidation with dilute nitric acid?
CHO COOH
H OH H OH
dil.HNO3
HO H HO H
H OH H OH
CH2OH COOH
Optically inactive
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Solutions of Assignment (Set-2) Biomolecules 269
14. (+) Arabinose is (2R, 3S, 4S)-aldopentose which of the following is (+) – arabinose?
CHO CHO
CHO CHO
H OH HO H
H OH H OH
HO H H OH
(1) H OH (2) (3) HO H (4)
HO H OH H OH
HO H H
CH2OH CH2OH
CH2OH CH2OH
Sol. Answer (2)
CHO
R
H OH
S
HO H
S
HO H
CH2OH
15. Peptides are composed of amino acids joined by amide bonds. which of the following statements is not correct?
(1) Amide group are more resistant to hydrolysis than one similar ester groups
(2) p- resonance stabilizes the amide bond
(3) Stable conformations of peptides are restricted to those having planar amide groups
(4) Amide groups do not participate in hydrogen bonding interaction
Sol. Answer (4)
Amide groups participate in H-bonding
16. A tripeptide is composed equally of L-valine, L-tyrosine and L-alanine (one molecule of each). How many
isomeric tripeptides of this kind may exist?
(1) 3 (2) 4 (3) 6 (4) 8
Sol. Answer (3)
Six tripeptides are possible from three different amino acids
17. Which of the following is an essential amino acid?
(1) Asparagine (2) Glutamine (3) Histidine (4) Alanine
Sol. Answer (3)
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270 Biomolecules Solutions of Assignment (Set-2)
29. The number of amino acids required to form a tripeptide bond are
(1) Seven (2) Two (3) Six (4) Four
Sol. Answer (4)
(1) Primary structure (2) Secondary structure (3) Tertiary structure (4) Quaternary structure
Sol. Answer (4)
(1) Fructose + Glucose (2) Fructose + Fructose (3) Glucose + Glucose (4) Glucose + Lactose
Sol. Answer (1)
(4) In cyclic structure of pyranose, there are five carbons and one oxygen atom
Sol. Answer (1)
40. In the double helix structure of DNA, the base pairs are
(1) Part of the backbone structure (2) Inside the helix
(3) Outside the helix (4) Bonded with covalent bond
Sol. Answer (2)
41. Cellulose upon acetylation with excess acetic anhydride / H2SO4 (catalytic) gives cellulose triacetate whose
structure is [IIT-JEE 2008]
AcO
AcO
AcO O O–
AcO O O– H H
H H AcO O OH H
AcO H H O H
O OAc H
H H O H O OH H
H H O H H OH
H O OAc H H OAc
(1) H O H (2) OH H
–O H H OH
OAc H H OAc
–O H
H OH
H OAc
H H O H H O H H O O– H H O H H O H H O O–
H H H H
(3) OAc H O OAc H
O
OAc H (4) H H O H H
O
H H
–O H –O H
H OAc H OAc H OAc OAc OAc OAc OAc OAc OAc
42. The correct statement about the following disaccharide is [IIT-JEE 2010]
CH2OH
O
H H CH2OH H
H O
OH H H OH
OCH2 CH2 O CH2OH
OH
H OH OH H
(a) (b)
(1) Ring (a) is pyranose with -glycosidic link (2) Ring (a) is furanose with -glycosidic link
(3) Ring (b) is furanose with -glycosidic link (4) Ring (b) is pyranose with -glycosidic link
Sol. Answer (1)
CH2OH
5 O
H H CH2OH H
H O
4 1
OH H H OH
O—CH2—CH2— O CH2OH
OH
3 2
H OH -linkage OH H
(a) (b)
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Solutions of Assignment (Set-2) Biomolecules 273
43. The following carbohydrate is [IIT-JEE 2011]
H OH
H O
HO OH
HO H HO
H
H
(1) A ketohexose (2) An aldohexose (3) An -furanose (4) An -pyranose
Sol. Answer (2)
OH
O
OH
HO
HO HO
— D — Glucopyranose, which is cyclic form of an aldohexose
SECTION - B
Objective Type Questions (More than one options are correct)
1. When D-Glucose reacts with three moles of phenylhydrazine it forms glucosazone. Which of the following
carbohydrates will give same osazone as that of D-Glucose?
CHO CHO
CH2OH CHO
O H OH HO H
HO H
H OH H OH
(1) HO H (2) HO H (3) (4)
HO H H OH
H OH H OH
HO H H OH
H OH H OH
CH2OH CH2OH CH2OH
CHO
Sol. Answer (1, 2)
During osazone formation, the reaction occurs only at C1 and C2 while rest of the molecule remains intact
since glucose and fructose differ from each other only in the arrangement of atoms at C1 and C2, therefore
they give same osazone.
O
Acetamide : — NH2 — C — NH2 —
n
O
||
Proteins peptide H2N — CH — C — NH — CH2 — COOH
|
CH3
Alany lg lycine
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274 Biomolecules Solutions of Assignment (Set-2)
CH2OH CH2OH
H O O
OH H H
H H
(1) OH H (2)
OH H
HO H HO OH
H OH H OH
H H
OH OH
HO HO
(3) O (4) O
HO HH HO
H
OH H
HO HO
H H
H HO
Sol. Answer (1, 3)
St-I is Howarth project ion while.
St-III is chair form of -D-Glucose
CH3 O HO O H H
(1) H2N — C — C — OH (2) H2N — C — C — OH (3) H2N — C — COOH (4) H2N — C — COOH
H (CH2—
)3 COOH (CH2—
)2 NH 2
N—H
N
Sol. Answer (2, 4)
In acidic medium N atom of –NH2 group absorb H+ and becomes +vely charged. +2 net charge will be present
on those amino acids which are having two basic amino groups.
H
OH
O O
O H H
(1) (2) OH
H O
OH OH
CH2OH CH2OH
O CH2OH H O
H H H H H OMe
(3) H (4)
OH H OH H
O CH2OH HO H
HO
H OH H OH
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Solutions of Assignment (Set-2) Biomolecules 275
6. Which of the following aldoses will give achiral product with NaBH4?
CHO
CHO CHO CHO
H OH
H OH H OH H OH
HO H
(1) HO H (2) HO H (3) HO H (4) HO H
HO H H OH H OH
H OH
H OH
CH2OH CH2OH CH2OH
CH2OH
Sol. Answer (2, 3)
CHO CH 2OH
H * OH H * OH
(1) HO H NaBH4 HO H
HO H HO H
CH2OH CH 2OH
(Chiral molecule)
CHO CH2OH
H * OH H OH
HO H NaBH4 HO H
(2)
HO H HO H
H OH H OH
CH2OH CH2OH
(Achiral)
CHO CH2OH
H * OH H OH
(3) HO H NaBH 4 HO H
H OH H OH
CH2OH CH2OH
(Achiral)
CHO CH2OH
H OH H * OH
HO H NaBH4 HO H
(4)
H OH H OH
H OH H OH
CH2OH CH2OH
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276 Biomolecules Solutions of Assignment (Set-2)
(4) Folding of polypeptide chain due to interaction between carbonyl group and — N — H group of peptide
linkage give rise to secondry structure
Sol. Answer (1, 4)
Primary or 1° structure of Protein
R1 O H O R3 O
H
N— C — C — N — C — C — N — C — C
H
R1 H R2 H H
Peptide bond Peptide bond
Secondary Structure
R1
H2N C
H C
H-Bond R4 O NH
H
C C
N H HC–R2
C H O
H C
O C N NH
R3 O
H-Bond R7 HC–R 5
C C
H H
H
N O N C
H O
C N
C H
O R6
H C R8
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Solutions of Assignment (Set-2) Biomolecules 277
11. The correct statement(s) about the following sugars X and Y is(are) [IIT-JEE-2009]
CH2OH
O
CH2OH CH2OH H H H
O O OH
O O H HO
H H H HOH2C H H H
O CH2OH H OH H
HO OH H H HO HO OH H
H OH OH H H OH
X Y
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278 Biomolecules Solutions of Assignment (Set-2)
Invert sugar
92 52
Specific rotation of invert sugar = 20
2
D-glucose on oxidation with Br2-water produces gluconic acid and not saccharic acid
SECTION - C
Linked Comprehension Type Questions
Comprehension-I
Carboxylic acids containing an amino group (—NH2) as a substituent are called amino acids. When this amino
group substitution is at -position with respect to carboxylic group, the aminoacid is called -amino acid. The
aminoacids with two carboxylic acids are called acidic amino acids whereas aminoacids with two amino group
are called basic amino acids. Aminoacids show amphoteric character. All chiral natural amino acids exist in L-
form.
1. Each of the following represent natural alanine (an amino acid) except
COOH COOH
COOH CH3
C C
(1) H2N H (2) HOOC H (3) H2N CH3 (4) H3C NH2
H H
CH3 NH2
Sol. Answer (4)
COOH COOH
O COOH O
(1) C — OH (2) H (3) H3C C H (4) H C H
OH
N
NH2
H CH2NH2 NH2
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Solutions of Assignment (Set-2) Biomolecules 279
3. What would be the net charge on the given amino acid at pH = 14?
COOH O
( CH2)—
H2N — C — 4 C — OH
COO O
| ||
H2N — C — (CH2 )4 — C — O
|
H
Comprehension-II
When either form of D-Glucose is dissolved in water, the solution gradually changes its optical rotation and
finally attains a constant optical rotation of +52º.
CHO CH2OH
CH2OH
O H OH O
H H H
OH HO H H
OH H H OH OH H
H HO OH
HO H OH
H OH H OH
CH2OH
(+ 19º) (+ 112º)
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280 Biomolecules Solutions of Assignment (Set-2)
Comprehension-III
Aldehydes and ketones are converted to acetals by treatment with an alcohol and a trace of acid catalyst.
These conditions also convert aldoses and ketoses to the acetals, call glycosides. In glycosides, an aglycone
is the group bonded to the anomeric carbon atom.
Example : Methanol is the aglycone in a methyl glycoside.
CH2OH
H O H
H CH3OH, H
2. (A)
OH H
OH OH
H OH
A is
(1) Methyl -D-glucopyranoside, -glycosidic bond
(2) Methyl -D-glucopyranoside, -glycosidic bond
(3) Methyl--D-glucopyranoside + methyl -D glucopyranoside
(4) No reaction can take place
Sol. Answer (3)
HOCH2 O O
H HO
H CH2OH
OH H
(1) Only -glycosidic linkage is present
(2) Only -glycosidic linkage is present
(3) -glycosidic linkage on glucose and -glycosidic linkage on fructose
(4) -glycosidic linkage on fructose and -glycosidic linkage on glucose
Sol. Answer (2)
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Solutions of Assignment (Set-2) Biomolecules 281
SECTION - D
Assertion-Reason Type Questions
1. STATEMENT-1 : Primary structure of proteins is determined by amino acid sequence.
and
STATEMENT-2 : Intramolecular hydrogen bonding between carbonyl group and N H group is responsible
for the folding of polypeptide chain.
STATEMENT-2 : Glucose is an aldose while fructose is a ketose (having keto functional group).
Sol. Answer (4)
Glucose and fructose can not be differentiated by Fehling solution because in alkaline medium an equilibrium
mixture of D-glucose, D-fructose, and D-mannose.
and
STATEMENT-2 : Enzymes are bio-catalyst and posses a stable configuration having a active site poket.
STATEMENT-2 : Reaction of glucose with Fehling’s solution gives CuO and gluconic acid. [IIT-JEE-2007]
Sol. Answer (3)
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282 Biomolecules Solutions of Assignment (Set-2)
SECTION - E
Matrix-Match Type Questions
1. Match the following
Column-I Column-II
(A) Glucose (p) Undergoes hydrolysis
(B) Fructose (q) React with Fehling solution
(C) Sucrose (r) React with Tollen’s reagent
(D) Maltose (s) Glycosidic linkage
Sol. Answer: A(q, r), B(q, r), C(p, q, r, s), D(p, q, r, s)
(A) Glucose can react with Fehling solution and Tollen’s reagent due to presence of –CHO group.
(B) Fructose can react with Fehling solution and Tollen’s reagent due to presence of –CHO group.
(C) Sucrose undergoes hydrolysis to give glucose and fructose.
Non reducing sugar so can not reduce Fehlng solution and Tollen’s reagent.
Glycosidic linkage is present
(D) Maltose undergoes hydrolysis to give glucose only
Due to free carbonyl group it is reducing hence reacts with Tollen’s reagent and Fehling
solution
glycosidic linkage is present.
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Solutions of Assignment (Set-2) Biomolecules 283
4. Match column-I with column-II
Column-I Column-II
(A) Glucose (p) React with Tollen’s reagent
(B) Fructose (q) React with Fehling reagent
(C) Sucrose (r) React with phenyl hydrazine to form osazone
(D) Maltose (s) It is a disachharide
(t) It is a furanose sugar
Sol. Answer: A(p, q, r), B(p, q, r, t), C(r, s), D(p, q, r, s)
SECTION - F
Integer Answer Type Questions
1. What is the total number of acidic amino acids found in human proteins?
Sol. Answer (2)
Aspartic acid and glutamic acids are acidic amino acids.
3. How many tripeptides are possible when Glycine, Alanine and Phenylalanine are allowed to form peptide bonds?
Sol. Answer (6)
Fact
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284 Biomolecules Solutions of Assignment (Set-2)
4. The iso-electric point of the given amino acid is, HO – C – CH2 – CH2 – CH – COOH (pKa = 2)
(pKa = 4) +
NH3(pKa = 9)
Sol. Answer (3)
6. The total number of basic groups in the following form of lysine is [IIT-JEE-2010]
Basic site
7. A decapeptide (Mol. Wt. 796) on complete hydrolysis gives glycine (Mol. Wt. 75), alanine and phenylalanine.
Glycine contributes 47.0% to the total weight of the hydrolysed products. The number of glycine units present
in the decapeptide is [IIT-JEE-2011]
Sol. Answer (6)
A decapeptide will have (9) peptide linkage
Mass of hydrolyzed product is (796 + 162) gm/mole
0.47 958
Number of glycine molecule = 6
75
8. The substituents R1 and R2 for nine peptides are listed in the table given below. How many of these peptides are
positively charged at pH = 7.0? [IIT-JEE-2012]
H3N CH CO NH CH CO NH CH CO NH CH COO
H R1 R2 H
Peptide R1 R2
I H H
II H CH 3
III CH2 COOH H
IV CH 2CONH2 (CH 2)4NH2
V CH 2CONH2 CH 2CONH 2
VI (CH 2)4 NH2 (CH 2)4NH2
VII CH2 COOH CH 2CONH 2
VIII CH2OH (CH 2)4NH2
IX (CH 2)4 NH2 CH 3
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Solutions of Assignment (Set-2) Biomolecules 285
Sol. Answer (4)
When any group in R1 and R2 is basic group then amino acid is positively charged at pH = 7.0. So, answers
are peptide IV, VI, VIII and IX.
9. When the following aldohexose exists in its D-configuration, the total number of stereoisomers in its pyranose
form is [IIT-JEE-2012]
CHO
CH2
CHOH
CHOH
CHOH
CH2OH
CHO
CH2
CHOH
CHOH
CH2OH
CH2OH
O
H
HO *
OH C* are chiral carbon atoms. Hence total stereoisomers are 8.
*
* H
HO H
10. The total number of distinct naturally occurring amino acids obtained by complete acidic hydrolysis of the
peptide shown below is [JEE(Advanced)-2014]
O O H O H O H
N
N N N
N N N
N O
H CH2 O H O H CH2
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286 Biomolecules Solutions of Assignment (Set-2)
SECTION - G
Multiple True-False Type Questions
1. STATEMENT-1 : Glycine is an achiral amino acid.
STATEMENT-2 : pH of alanine is less than 7.
STATEMENT-3 : Almost all proteins are polypeptides.
(1) T T T (2) FFF (3) TFT (4) FTF
Sol. Answer (1)
Fact
SECTION - H
Aakash Challengers Questions
1. In a paper electrophoresis amino acids and peptides can be separated by their differential migration in an electric
field. To the center of a strip of paper, wet with buffer at pH = 6 is applied a mixture of the following three
peptides in a single small spot : Gly-Ala, Gly-Asp and Gly-Arg. A positively charged electrode (anode) is attached
to the left side of the paper and a negatively charged electrode (cathode) to the rightside. A voltage is applied
across the ends of the paper for a time, after which the peptides have separated into three spots. One near the
location of the original spot which peptide is in each spot? Explain.
Sol. Gly-Asp will move towards Anode while Gly-Arg will move towards cathode and Gly-Ald will remain hear spot.
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Solutions of Assignment (Set-2) Biomolecules 287
2. Starch consist of amylose and amylopectin structure of amylopectin is given as below
H
CH2OH
O
O H
H H
H
HO OH CH2OH
O
H O H
H H
HO OH
H
O
H CH2
O
O H
H H
HO OH
H O
In structure of amylopectin
(1) -1,4-glycosidic bonds (2) -1,6-glycosidic bonds
(3) -1,4-glycosidic bonds (4) -1,4-glycosidic bonds and -1,6-glycosidic bonds
Sol. Answer (4)
In amylo pectin, -1,4 and -1,6 linkage that provides the attachment point for another chain.
CHO
H OH
HO H
HO H
H OH
CH2OH
(D-galactose)
CH2OH CH2OH O
O
HO HO
OCH3 H
(1) (2) HO
HO OH OH
H OCH3
HO HO
CH2OH CH2OH O
O
(3) OCH3 (4) H
HO OH HO OH
H OCH3
Sol. Answer (4)
OH CH2OH
HO H
OH OCH3
-D-Galctopyranoside
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288 Biomolecules Solutions of Assignment (Set-2)
4. Which of the following statements would correctly describe the isoelectric point of cysteic acid an oxidation
product of cysteine?
H
C
H3N COOH
CH2
SO3
Cysteic acid
(1) Lower than that of aspartic acid (2) About the same as that of aspartic acid
(3) About the same as that of Cysteine (4) Higher than that of lysine
Sol. Answer (1)
5. Which two of the following compounds are reduced to the chiral alditol by NaBH4?
H OH H OH H OH HO H
H OH HO H HO H H OH
HO H HO H H OH H OH
A biomolecule R
The biomolecule R binds to a tripeptide because its binding site is complementry to that of tripeptide. The shape
of the tripeptide would be
Note : Complimentarity in the figure is shown by shape
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Solutions of Assignment (Set-2) Biomolecules 289
Sol. Answer (4)
Tripeptide will exactly fit into the binding site due to exact complimentarity of shape.
7. A mixture of three amino acids X-(pH = 3.2), Y-(pH = 5.7) and Z-(pH = 9.7) under electrophoresis at
pH = 7.7, in which direction will each component of the mixture move?
CHO CN COOH
H OH HO H (i) Ba (OH)2
HO H
Sol. aq. HCN
H OH H OH (i) H2SO4
H OH
CH 2OH H OH H OH
CHO CO
HO H HO H
Na/Hg O
H OH H OH
H2SO4
H OH H
CH2OH CH 2OH
D-arabinose
10. -glucopyranose is oxidised by HIO4 more rapidly than the -anomer at the 1,2 bond. Suggest a reason.
Sol. -glucopyranose is cis-1, 2-diol and the -anomer is the trans 1, 2 diol. Since the former can form a cyclic
ester with periodic acid and latter can not, the former is oxidised more rapidly than the latter.
11. Calculate how much of the -anomer and -anomers are present in an equilibrium mixture with a specific rotation
of +52.6º?
Sol. Answer
-anomer 36%
-anomer 64%
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290 Biomolecules Solutions of Assignment (Set-2)
12. Compound (A) C5H10O5, give a tetra-acetate with Ac2O and oxidation of (A) with Br2–H2O gives an acid, C5H10O6.
Reduction of (A) with HI and red phosphorous gives 2-methyl butane. What is the structure of (A)?
Sol. Answer
CHO
CHOH
HO– CH2–C–OH
CH2O H
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