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Carbohydrates

1 Which of the following is a D-aldopentose?




2. Which of the following is an L-saccharide?


3 (+)-Arabinose is (2R, 3S, 4S)-aldopentose. Which of the following is (+)-arabinose?


4 Which of the following gives an optically inactive aldaric acid on oxidation with dilute nitric acid?


5 Which two of the following compounds are reduced to the same chiral alditol by sodium borohydride?

A) 1 & 2 B) 2 & 3 C) 3 & 4 D) 2 & 3

6 Which of the following statements is correct?
A) The Ruff procedure lengthens an aldose chain and gives a single product.
B) The Ruff procedure shortens an aldose chain and gives two epimers.
C) The Kiliani-Fischer procedure shortens an aldose chain and gives a single product.
D) The Kiliani-Fischer procedure lengthens an aldose chain and gives two epimers.

7 Which two of the following compounds, if any, are epimers?

A) 1 & 4 B) 1 & 3 C) 2 & 3 D) 3 & 4

8 Which of the following is not a disaccharide?
A) sucrose B) mannose C) lactose D) maltose

9 Which of the following is not a reducing sugar?
A) sucrose B) mannose C) lactose D) fructose

10 Which two of the following aldohexoses give the same osazone derivative?

A) 1 & 4 B) 1 & 3 C) 2 & 3 D) 3 & 4

11 Which statement about the pyranose form of mannose is not correct?
A) it exists as two anomeric stereoisomers.
B) it reacts with Tollens' reagent to give a silver mirror. (i.e. it is a reducing sugars)
C) reaction with excess CH
3
I and AgOH gives a non-reducing penta-O-methyl derivative.
D) it resists reduction with aqueous sodium borohydride.

12 Two aldopentoses X and Y give the same osazone derivative. X is oxidized to an optically active
aldaric acid by dilute nitric acid. Ruff degradation of Y gave a tetrose which was similarly oxidized to an
optically active aldaric acid Assign the structures of X and Y from the following list?

A) X=1 & Y=4 B) X=4 & Y=1 C) X=2 & Y=3 D) X=3 & Y=2
13 Which of the structures 1 through 4 is methyl -D-
galactopyranoside?


A 1


B 2


C 3


D 4


14 What is invert sugar, and why is it so named?
A) the sugar mixture from hydrolysis of sucrose; fructose is isomerized to glucose.
B) the sugar mixture from hydrolysis of sucrose; the optical rotation changes from (+) to (-).
C) the sugar mixture from hydrolysis of starch; -glycosidic bonds are changed to -glycosidic
bonds.
D) the sugar mixture from hydrolysis of starch; glucose is isomerized to fructose.

15 Which of the following compounds is a -aldopentafuranose?




A 1


B 2


C 3


D 4


16 Which of the following compounds is a -ketohexafuranose?



A 1 B 2 C 3 D 4


17 Which of the following disaccharides is the -anomer of 4-O-( -D-glucopyranosyl)-D-
glucopyranose?




A 1


B 2


C 3


D 4


18 Which of the following disaccharides is a nonreducing sugar (does not react with Tollens' reagent)?




A 1


B 2


C 3


D 4


19 Which of the following best describes the polysaccharide amylose?
A) a 1,4-O--linked poly-D-glucose B) a 1,4-O--linked poly-D-glucose
C) an alternating 1,4-O-/-linked poly-D-glucose D) a 1,4-O--linked poly-D-mannose

20 Which of the following disaccharides is the -anomer of 4-O-( -D-glucopyranosyl)-D-
glucopyranose?




A 1


B 2


C 3


D 4


21 Which of the following best describes the polysaccharide cellulose?
A) a 1,4-O--linked poly-D-galactose B) a 1,4-O--linked poly-D-galactose
C) a 1,4-O--linked poly-D-glucose D) a 1,4-O--linked poly-D-glucose

22 When octa-O-methyl D-cellobiose is hydrolyzed by aqueous acid, two O-methyated glucose
derivatives are formed.
One is a tetramethyl derivative, and the other is a trimethyl derivative.
Why is a single methyl substituent lost in this process?
A) one methoxy group is lost by -elimination.
B) one methoxy group is an ester and the others are all ethers.
C) one methoxy group is part of an acetal, the others are all ethers.
D) one glucose is an -methyl glycoside; the other is a -methyl glycoside.

23 Gentiobiose (C
12
H
22
O
11
) is a reducing sugar. It forms an osazone derivative and mutarotates.
Hydrolysis of gentiobiose by the enzyme emulsin produces D-glucose as the only product.
An octamethyl derivative of gentiobiose is hydrolyzed to a mixture of 2,3,4,6-tetra-O-methylglucose and
2,3,4-tri-O-methylglucose. What is the structure of gentiobiose (either anomer)?




A 1


B 2


C 3


D 4


24 Trehalose (C
12
H
22
O
11
) is a non-reducing sugar. Hydrolysis by the enzyme maltase produces D-glucose
as the only product.
An octamethyl derivative of trehalose is hydrolyzed to 2,3,4,6-tetra-O-methylglucose as the only
product. What is the structure of trehalose?




A 1


B 2


C 3


D 4


25 Acid-catalyzed reaction of D-glucose with benzaldehyde produces the 4,6-O-benzylidene derivative.
Reduction with NaBH
4
, followed by excess HIO
4
cleavage and acid hydrolysis yields a C
4
H
8
O
4
tetrose
and benzaldehyde.
What is the configuration of this tetrose?
A) 2S, 3S B) 2R, 3S C) 2R, 3R D) 2S, 3R

26 A D-aldohexose gives an optically inactive aldaric acid on oxidation with nitric acid.
Ruff degradation of this aldohexose produces an aldopentose that is reduced by NaBH
4
to an optically
active alditol.
Which of the following is this hexose?



A 1


B 2


C 3


D 4


27 Mycarose is a rare C
7
H
14
O
4
sugar found in some antibiotic natural products.
Mycarose gives a positive Tollens' test, does not form an osazone derivative, and on exhaustive
HIO
4
oxidation gives HCO
2
H, CH
3
CHO and CH
3
COCH
2
CHO.
Which of the following structures might be mycarose?



A 1


B 2


C 3


D 4


28 If two isomers have been classified correctly as anomers, they may also be called...?
A) conformers
B) enantiomers
C) tautomers
D) diastereomers

Amino Acids with Hydrophobic Side Chain - Aliphatic


Alanine, Ala, A

Isoleucine, Ile, I

Leucine, Leu, L

Valine, Val, V
back to top
Amino Acids with Hydrophobic Side Chain - Aromatic



Phenylalanine, Phe, F

Tryptophan, Trp, W

Tyrosine, Tyr, Y

back to top
Amino Acids with Polar Neutral Side Chains



Asparagine, Asn, N

Cysteine, Cys, C

Glutamine, Gln, Q


Methionine, Met, M

Serine, Ser, S

Threonine, Thr, T

back to top
Amino Acids with Electricaly Charged Side Chains - Acidic



Aspartic acid, Asp, D

Glutamic acid, Glu, E

back to top
Amino Acids with Electricaly Charged Side Chains - Basic



Arginine, Arg, R

Lysine, Lys, K

Histidine, His, H
back to top
Unique Amino Acids



Glycine, Gly, G

Proline, Pro, P

back to top
Properties of Common Amino Acids




- See more at: http://www.sigmaaldrich.com/life-science/metabolomics/learning-center/amino-acid-reference-


AMYLOSE AMYLOPECTIN CELLULOSE GLYCOGEN
Monosaccharide -glucose -glucose -glucose -glucose
Type(s) of bond -1,4 glycosidic -1,4 glycosidic and some 1,6 at
branches
-1,4 glycosidic -1,4 glycosidic with a-1,6 at
branches
Overall shape of molecule helix branched straight chain branched, slightly coiled (more
branched than amylopectin)
Hydrogen bonding within or
between molecules
Hydrogen bonds between sugar
units in the chain
Some hydrogen bonds between sugar
units in the chain
Hydrogen bonds between sugar
units in different chains
Some hydrogen bonds between sugar
units in the chain
Solubility in water Insoluble Insoluble Insoluble Insoluble
Function Energy store in plants Energy store in plants Plant structural role (cell walls) Energy store in animals




AS-LevelBiological MoleculesBiologyOCR




This color wheel demonstrates which color a compound will appear if it only has one absorption in
the visible spectrum. For example, if the compound absorbs red light, it will appear green.
absorbed versus color observed
400 nm Violet absorbed, Green-yellow observed ( 560 nm)
450 nm Blue absorbed, Yellow observed ( 600 nm)
490 nm Blue-green absorbed, Red observed ( 620 nm)
570 nm Yellow-green absorbed, Violet observed ( 410 nm)
580 nm Yellow absorbed, Dark blue observed ( 430 nm)
600 nm Orange absorbed, Blue observed ( 450 nm)
650 nm Red absorbed, Green observed ( 520 nm)



Crystal field splitting diagrams[edit]

Crystal field splitting diagrams (-acceptor ligands)
Octahedral Pentagonal bipyramidal Square antiprismatic



Square planar Square pyramidal Tetrahedral



Trigonal
bipyramidal




The spectrochemical series is an empirically-derived list of ligands ordered by the size of the splitting
that they produce (small to large ; see also this table):
I

< Br

< S
2
< SCN

< Cl

< NO
3

< N
3

< F

< OH

< C
2
O
4
2
< H
2
O < NCS

< CH
3
CN < py < NH
3
<
en < 2,2'-bipyridine < phen < NO
2

< PPh
3
< CN

< CO
Field Splitting Energies for Some Octahedral (".
Table 23.10 Crystal Field Splitting Energies for Some Octahedral (o)* and Tetrahedral
(t) Transition-Metal Complexes
Octahedral
Complexes

o
(cm
1
)
Octahedral
Complexes

o
(cm
1
)
Tetrahedral
Complexes

t
(cm
1
)
[Ti(H
2
O)
6
]
3+
20,300 [Fe(CN)
6
]
4
32,800 VCl
4
9010
[V(H
2
O)
6
]
2+
12,600 [Fe(CN)
6
]
3
35,000 [CoCl
4
]
2
3300
[V(H
2
O)
6
]
3+
18,900 [CoF
6
]
3
13,000 [CoBr
4
]
2
2900
[CrCl
6
]
3
13,000 [Co(H
2
O)
6
]
2+
9300 [CoI
4
]
2
2700
[Cr(H
2
O)
6
]
2+
13,900 [Co(H
2
O)
6
]
3+
27,000

[Cr(H
2
O)
6
]
3+
17,400 [Co(NH
3
)
6
]
3+
22,900

[Cr(NH
3
)
6
]
3+
21,500 [Co(CN)
6
]
3
34,800

[Cr(CN)
6
]
3
26,600 [Ni(H
2
O)
6
]
2+
8500

Cr(CO)
6
34,150 [Ni(NH
3
)
6
]
2+
10,800

[MnCl
6
]
4
7500 [RhCl
6
]
3
20,400

[Mn(H
2
O)
6
]
2+
8500 [Rh(H
2
O)
6
]
3+
27,000

Octahedral
Complexes

o
(cm
1
)
Octahedral
Complexes

o
(cm
1
)
Tetrahedral
Complexes

t
(cm
1
)
[MnCl
6
]
3
20,000 [Rh(NH
3
)
6
]
3+
34,000

[Mn(H
2
O)
6
]
3+
21,000 [Rh(CN)
6
]
3
45,500

[Fe(H
2
O)
6
]
2+
10,400 [IrCl
6
]
3
25,000

[Fe(H
2
O)
6
]
3+
14,300 [Ir(NH
3
)
6
]
3+
41,000

*Energies obtained by spectroscopic measurements are often given in units of wave numbers (cm
1
);
the wave number is the reciprocal of the wavelength of the corresponding electromagnetic radiation
expressed in centimeters: 1 cm
1
= 11.96 J/mol.
Source of data: Duward F. Shriver, Peter W. Atkins, and Cooper H. Langford, Inorganic
Chemistry, 2nd ed. (New York: W. H. Freeman and Company, 1994).

Colours of Various Example Coordination Complexes
Fe
2+
Fe
3+
Co
2+
Cu
2+
Al
3+
Cr
3+

Hydrated
Ion
[Fe(H
2
O)
6
]
2+

Pale green
Solution
[Fe(H
2
O)
6
]
3+

Yellow/brown
Solution
[Co(H
2
O)
6
]
2+

Pink
Solution
[Cu(H
2
O)
6
]
2+

Blue
Solution
[Al(H
2
O)
6
]
3+

Colourless
Solution
[Cr(H
2
O)
6
]
3+

Green
Solution
OH

, dilute
[Fe(H
2
O)
4
(O
H)
2
]
Dark green
Precipitate
[Fe(H
2
O)
3
(O
H)
3
]
Brown
Precipitate
[Co(H
2
O)
4
(O
H)
2
]
Blue/green
Precipitate
[Cu(H
2
O)
4
(OH)
2
]
Blue
Precipitate
[Al(H
2
O)
3
(O
H)
3
]
White
Precipitate
[Cr(H
2
O)
3
(O
H)
3
]
Green
Precipitate
OH

,
concentrat
ed
[Fe(H
2
O)
4
(O
H)
2
]
Dark green
Precipitate
[Fe(H
2
O)
3
(O
H)
3
]
Brown
Precipitate
[Co(H
2
O)
4
(O
H)
2
]
Blue/green
Precipitate
[Cu(H
2
O)
4
(OH)
2
]
Blue
Precipitate
[Al(OH)
4
]


Colourless
Solution
[Cr(OH)
6
]
3

Green
Solution
NH
3
, dilute
[Fe(H
2
O)
4
(O
H)
2
]
Dark green
Precipitate
[Fe(H
2
O)
3
(O
H)
3
]
Brown
Precipitate
[Co(H
2
O)
4
(O
H)
2
]
Blue/green
Precipitate
[Cu(H
2
O)
4
(OH)
2
]
Blue
Precipitate
[Al(H
2
O)
3
(O
H)
3
]
White
Precipitate
[Cr(H
2
O)
3
(O
H)
3
]
Green
Precipitate
NH
3
,
concentrat
ed
[Fe(H
2
O)
4
(O
H)
2
]
Dark green
Precipitate
[Fe(H
2
O)
3
(O
H)
3
]
Brown
Precipitate
[Co(NH
3
)
6
]
2+

Straw
coloured
Solution
[Cu(NH
3
)
4
(H
2
O)
2
]
2+

Deep blue
Solution
[Al(H
2
O)
3
(O
H)
3
]
White
Precipitate
[Cr(NH
3
)
6
]
3+

Green
Solution
CO
3
2

FeCO
3

Dark green
Precipitate
[Fe(H
2
O)
3
(O
H)
3
]
Brown
Precipitate +
bubbles
CoCO
3

Pink
Precipitate
CuCO
3

Blue/green
Precipitate

Colors of Lanthanide complexes[edit]

Schematic representation of d-level
splitting


In the formation of an octahedral complex, ligands approach the central atom
or ion along the x, y, and z axes. Maximum interference occurs with the dz2
and dx2-y2 orbitals (shown in yellow). The energies of these orbitals are
raised with respect to those of the dxy, dxz, and dyz orbitals (shown in red).


Table 16.5 A Summary of Types of Complexes Formed by First-Row Metal Ions .
Number of d
Electrons Most Common Ion Usual Geometry b Hybrid Orbital Example
0 Sc 3 _ Octahedral d 2 sp 3 Sc(H 2 O) 6 3 _
1 Ti 3 _ Octahedral d 2 sp 3 Ti(H 2 O) 6 3 _
2 V 3 _ Octahedral d 2 sp 3 VF 6 3 _
3 Cr 3 _ Octahedral d 2 sp 3 Cr(NH 3 ) 6 3 _
4 a Mn 3 _ Octahedral (h.s.) sp 3 d 2 Mn(H 2 O) 6 3 _
4 a Mn 3 _ Octahedral (l.s.) d 2 sp 3 Mn(CN) 6 3 _
5 Fe 3 _ Octahedral (h.s.) sp 3 d 2 Fe(H 2 O) 6 3 _
5 Fe 3 _ Octahedral (l.s.) d 2 sp 3 Fe(CN) 6 3 _
5 Fe 3 _ Tetrahedral sp 3 FeCl 4 _
6 Co 3 _ Octahedral (h.s.) sp 3 d 2 CoF 6 3 _
6 Co 3 _ Octahedral (l.s.) d 2 sp 3 Co(H 2 O) 6 3 _
7 Co 2 _ Octahedral (h.s.) sp 3 d 2 Co(H 2 O) 6 2 _
7 Co 2 _ Trigonal bipyramid dsp 3 Co(CN) 5 3 _
7 Co 2 _ Tetrahedral sp 3 CoCl 4 2 _
7 Co 2 _ Square planar dsp 2 Co(CN) 4 2 _
8 Ni 2 _ Tetrahedral sp 3 Ni(NH 3 ) 4 2 _
8 Ni 2 _ Octahedral sp 3 d 2 Ni(NH 3 ) 6 2 _
8 Ni 2 _ Trigonal bipyramid dsp 3 Ni(CN) 5 3 _
8 Ni 2 _ Square base pyramid sp 2 d 2 Ni(CN) 5 3 _
8 Ni 2 _ Square planar dsp 2 Ni(CN) 4 2 _
9 a Cu 2 _ Octahedral sp 3 d 2 CuCl 6 4 _
9 a Cu 2 _ Tetrahedral sp 3 Cu(NH 3 ) 4 2 _
10 Zn 2 _ Octahedral sp 3 d 2 Zn(H 2 O) 6 2 _5 Multiple Choice Questions
1. hexacyanoferrate(II)
a. [Co(NH)]Cl
b. Fe(CN)
c. K [Fe(CN)]
d. Ru(NH)Cl
triethylenediamminemanganese(II)
. Ru(NH)Cl
a. Mn(NHCHCHNH)
b. [Co(NH)Cl]Cl
c. [Fe(en)(NO)]SO
potassium hexacyanoferrate(III)
. K[Fe(CN)]
a. Fe(CN)
b. K[PtCl]
c. K[PtCl]
hexaamminecobalt(II) chloride
. [Co(NH)Cl]Cl
a. [Co(HO)]I
b. [Co(NH)]Cl
c. Ru(NH)Cl
[Cr(NH)NHCHCHNHCl]I
. triamminechloroethylenediamminechromium(III) iodide
a. sodium dicyanobis(oxalato)ferrate(III)
b. triamminebromoplatinum(II) chloride
c. aquatricarbonylplatinum(II) bromide
5 True/False Questions
1. K[PtCl] potassium tetrachloroplatinumate(II)
True False
2. [Co(NH)Cl]Cl pentaamminechlorocobalt(III) chloride
True False
3. [Co(HO)]I hexaaquacobalt(III) iodide
True False
4. [Fe(en)(NO)]SO hexaaquacobalt(III) iodide
True False
5. Ru(NH)Cl pentaamminechlorocobalt(III) chloride
True False

10 Zn 2 _ Tetrahedral sp 3 Zn(NH 3 ) 4 2 _
10 Ag _ Linear sp Ag(NH 3 ) 2 _
Based on CO IR stretching frequencies, the following ligands can be
ranked from best -acceptor to worst:
NO+ > CO > PF3 > RN