Chem Imp
Chem Imp
Chem Imp
MAHENDRA KALRA
NAME OF STUDENT
K.V.ITARANA
• Step II: The carbocation at once combines with the nucleophile to form final product.
2. In the following pairs of halogen compounds, which would undergo SN2 reaction faster?
Answer: ( 1st one is faster It is primary halide and therefore undergoes SN2 reaction faster.)
(1st one is faster As iodine is a better leaving group because of its large size, it will be released at a faster rate in
th presence of incoming nucleophile)
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3. Predict the order of reactivity of the following compounds:
(i)The four isomeric bromobutanes (SN1)
(ii) C6H5CH2Br, C6H5CH (C6H5) Br, C6H5CH (CH3) Br, C6H5C(CH3)(C6H5)Br (SN2)
Answer: (i) CH3CH2CH2CH2Br < (CH3)2CHCH2Br < CH3CH2CH(Br)CH3 < (CH3)3CBr (SN1)
(ii) CH3CH2CH2CH2Br > (CH3)2CHCH2Br > CH3CH2CH(Br)CH3 > (CH3)3CBr (SN2)
4. Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism?
Explain your answer.
Answer:
5. In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
Answer:
6. Which compound in each of the following pairs will react faster in SN2 reaction with –OH? (i) CH3Br or CH3I
(ii) (CH3)3CCl or CH3Cl Answer: (i) CH3I (ii) CH3Cl
7. Write the mechanism of the following reaction:
Answer:
8. Arrange the compounds of each set in order of reactivity towards SN2 displacement
(i) 2-Bromo-2-methylbutane, 1-Bromopentane , 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane
Answer: (i) 1-Bromopentane >2-Bromopentane>2-Bromo-2-methylbutane
(ii) 1-Bromo-3-methylbutane > 3-Bromo-2-methylbutane >2-Bromo-2-methylbutane
(iii) 1-Bromobutane>1-Bromo-3-methylbutane >1-Bromo-2-methylbutane>1-Bromo-2,2-dimethylpropane
UNIT: 11 ALCOHOLS,PHENOLS & ETHERS
1. Mechanism for the Hydration of alkenes
Mechanism
The mechanism of the reaction involves the following three steps:
Step 1: Protonation of alkene to form carbocation by electrophilic attack of H3O+.
Mechanism
Step 1: Formation of protonated alcohol.
Step 2: Formation of carbocation: It is the slowest step and hence, the rate determining step of the reaction.
The acid used in step 1 is released in step 3. To drive the equilibrium to the right, ethene is removed as it is formed.
Mechanism
When HI is in excess and the reaction is carried out at high temperature, ethanol reacts with another molecule of
HI and is converted to ethyl iodide.
Answers:1 & 2
• Mechanism - Nucleophile attacks electrophilic sp2 hybridised carbon. the hybridization changes to sp3 and a
tetrahedral alkoxide intermediate is formed which reacts with proton to form addition product.
•
3.
• (i),Butanone. Propanone Propanal, Ethanal
• (ii) Acetophenone , p-Tolualdehyde ,Benzaldehyde, p-Nitrobenzaldehyde ,.
• (iii)Di-tert-butyl ketone, Methyl tert-butyl ketone, Acetone, Acetaldehyde
5. Fehling’s test:
• [Only Aliphatic Aldehydes(e.g.Ethanal,Propanal etc)
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• Fehling’s reagent: Fehling solution A is aqueous copper sulphate and Fehling solution B is alkaline sodium
potassium tartarate (Rochelle salt)
• Test: On heating an aldehyde with Fehling’s reagent,(equal amount of Fehling solution A & Fehling solution B )a
reddish brown precipitate of [Cu2O] is obtained.
• Reaction:R CHO + 2 Cu2+ + 5 OH¯ → RCOO¯ + Cu2O + 3 H2O
Aldehyde Red ppt
O
||
R – C – R + Fehling solution → No red ppt.
Important Note: Ketones do not give this test & also Aromatic aldehyde do not reduce fehling solution
4. Tollens test [Aliphatic Ammoniacal . Bright silver mirror [Ag] is produced due
Aldehydes(e.g.Ethanal,Propa AgNO3 to the formation of silver metal.
nal etc) & Aromatic
Aldehydes (Benzaldehyde
etc.)]
5. Fehling’s test [Only Fehling solution A Reddish brown precipitate of [Cu2O] is
Aliphatic Aldehydes] (aqueous copper obtained.
sulphate & Fehling
solution B alkaline
sodium potassium
tartarate(Rochelle
salt)
6. Iodoform test (Aldehydes & I2 / NaOH Yellow Ppt of CHI3 .is formed
Ketones containing –COCH3
linkage)
10. Azo dye test(Aniline) (NaNO2 + HCl Reaction with NaNO2 + HCl at 273-278 K
)[Nitrous acid] gives BDC which forms a brilliant orange
followed by - Azo dye with -napthol in sodium
napthol hydroxide
11. Test for Methanoic acid Amm . AgNO3 & Bright silver mirror [Ag] is produced due
(Formic acid) Fehling solution A&B to the formation of silver metal
Tollens test & Fehling’s Reddish brown precipitate of [Cu2O] is
test obtained.
4. Finkelstein reaction: Alkyl chlorides/ bromides on reaction with NaI in dry acetone to give Alkyl iodides.
R – Cl +NaI ⎯acetone
⎯⎯→ R – I + NaCl
R – Br +NaI ⎯⎯⎯→ R – I + NaBr
acetone
5. Swarts reaction Heating of alkyl chloride/bromide in the presence of a metallic fluoride such as AgF, Hg2F2, CoF2
or SbF3 to give alkyl fluorides R – X ⎯⎯ ⎯2⎯ ⎯ ⎯ ⎯→ R – F example :
AgF, Hg F2 , CoF2 or SbF3
13. Williamson’s synthesis :In this method an alkyl halide (Better results are obtained if the alkyl halide is primary)
reacts with a sodium alkoxide to form symmetrical or unsymmetrical ethers.
• Limitation In case of secondary and tertiary alkyl halides, elimination competes over substitution. If a tertiary alkyl
halide is used, an alkene is the only reaction product and no ether is formed. For example, the reaction of CH3ONa
with (CH3)3C–Br gives exclusively 2-methylpropene. It is because alkoxides are not only nucleophiles but strong
bases as well. They react with alkyl halides leading to elimination reactions.
17. Cross Aldol Condensation: When aldol condensation is carried out between two different aldehydes and / or
ketones, it is called cross aldol condensation. If both of them contain α-hydrogen atoms, it gives a mixture of
four products.
19. Clemmensen Reaction: The carbonyl group of aldehydes and Ketones are reduced to CH2 group on treatment
with zinc amalgam(Zn/Hg) and concentrated hydrochloric acid.(Conc.HCl)
⎯− Hg
Example: CH3CH =O ⎯Zn ⎯, HCl
⎯→ CH3CH3
⎯− Hg
CH3CO CH3 ⎯Zn ⎯, HCl
⎯→ CH3CH2CH3
21. Rosenmund Reaction:Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium
sulphate. RCOCl + H2 ⎯ ⎯→ RCHO + HCl
25. Ozonolysis of alkenes involves the addition of ozone molecule to alkene to form ozonide, and then cleavage of
the ozonide by Zn-H2O to Aldehyde and/or Ketones.
26. Esterification: Esters are generally prepared by heating carboxylic acids with alcohols in the presence of a
mineral acid such as conc. H2SO4 or HCl gas.
27. Decarboxylation : Sodium salts of acids when heated with soda lime, alkanes are formed.
28. Hell Volhard Zelinsky: Carboxylic acids having an α-hydrogen are halogenated at the α-position on treatment
with chlorine or bromine in the presence of small amount of red phosphorus to give α-halocarboxylic acids
29. Acetylation: The introduction of acetyl (CH3CO) group in alcohols or phenols is known as acetylation.
UNIT: 13 AMINES
32. Ammonolysis
33. Carbylamine reaction(Isocyanide test):Aliphatic and aromatic primary amines on heating with chloroform
and ethanolic potassium hydroxide form isocyanides or carbylamines which are foul smelling substances.
R − NH 2 + CHCl3 + 3KOH ⎯⎯ ⎯
heat
→ R − NC + 3KCl + 3H 2O
34. Diazotization :
35. Sandmeyers reaction:The Cl–, Br– and CN– nucleophiles can easily be introduced in the benzene ring in the
presence of Cu(I) ion[cuprous chloride or cuprous bromide or cuprous cyanide]
.
36. Gatterman reaction:Chlorine or bromine can also be introduced in the benzene ring by treating the diazonium
salt solution with corresponding halogen acid in the presence of copper powder
37. Coupling reaction:Benzene diazonium chloride reacts with phenol in which the phenol molecule at its para
position is coupled with the diazonium salt to form p-hydroxyazobenzene.. Similarly the reaction of diazonium
salt with aniline yields p-aminoazobenzene.
39. Benzoylation: Amines reacts with benzoyl chloride (C6H5COCl) to form N Alkylbenzamide
2. Give the IUPAC names of the following compounds:(i) CH3CH(Cl)CH(Br)CH3 (ii) CHF2CBrClF (iii) ClCH2C≡CCH2Br
(iv) (CCl3)3CCl
3. Write IUPAC names of the following:
a. CH3)2CHNH2 e. C6H5NHCH3
b. CH3(CH2)2NH2 f. CH3CH2)2NCH3
c. CH3NHCH(CH3)2 g. m–BrC6H4NH2
d. (CH3)3CNH2
10. Classify the following amines as primary, secondary or tertiary:
Write the reactions and the conditions involved in the conversion of:
1. Chloroethane to butane 9. Propene to Propan-2-ol
2. 2-Chlorobutane to 3, 4-dimethylhexane 10. Phenol to Salicylic acid
3. Benzene to diphenyl 11. Phenol to Salicylaldehyde
4. Bromopropane to Iodopropane 12. Ethanal to 3-Hydroxybutanal
5. Bromopropane to Flouropropane 13. Ethanal to But-2-enal
6. 1-Bromopropane to 2-bromopropane 14. Benzaldehyde to Toluene
7. 2-Bromopropane to 1-bromopropane 15. Propanal to Propane
8. Propene to Propan-1-ol 16. Acetone to Propane
2. 2
3. What happens when (i) n-butyl chloride is treated with alcoholic KOH, (ii) bromobenzene is treated with Mg in
the presence of dry ether, (iii) chlorobenzene is subjected to hydrolysis, (iv) ethyl chloride is treated with
aqueous KOH, (v) methyl bromide is treated with sodium in the presence of dry ether, (vi) methyl chloride is
treated with KCN?
4. Write structures of the products of the following reaction:
(iii)
9. Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents. (i) PhMgBr and then
H3O+ (ii)Tollens’ reagent (iii) Semicarbazide and weak acid (iv)Excess ethanol and acid (v) Zinc amalgam and
dilute hydrochloric acid
10. Write the structures of products of the following reactions
11. Complete each synthesis by giving missing starting material, reagent or products
a)
b)
c)
d)
e)
f)
g)
h)
i)
j) CH3CN A B
k) CH3COOH A B C
17. Write structures and IUPAC names of (i) the amide which gives propanamine by Hoffmann bromamide reaction.
(ii) the amine produced by the Hoffmann degradation of benzamide.
18. Write chemical equations for the following reactions: (i) Reaction of ethanolic NH3 with C2H5Cl. (ii) Ammonolysis
of benzyl chloride and reaction of amine so formed with two moles of CH3Cl.
19. An aromatic compound A on treatment with aqueous ammonia and heating forms compound B which on heating
with Br2 and KOH forms compound C of molecular formula C6H7N .Write the structures and IUPAC names of
compounds A,B,C
20. Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.
21. Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which
neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction. (i)
Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1-
Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2, 2-Dimethylbutanal
7. Anomers: The two cyclic hemiacetal forms of glucose differ only in the configuration of the hydroxyl group at C1,
called anomeric carbon (the aldehyde carbon before cyclisation). Such isomers, i.e., α-form and β-form, are called
anomers.
8. The open chain structure could not following reactions: Despite having the aldehyde group, glucose does not
give 2,4-DNP test, Schiff’s test and it does not form the hydrogensulphite addition product with NaHSO3.
9. All proteins are polymers of α-amino acids. Amino acids contain amino (–NH2) and carboxyl (–COOH) functional
groups.
10. Amino acids are classified as acidic, basic or neutral depending upon the relative number of amino and carboxyl
groups in their molecule. Equal number of amino and carboxyl groups makes it neutral; more number of amino
than carboxyl groups makes it basic and more carboxyl groups as compared to amino groups makes it acidic.
11. The amino acids, which can be synthesised in the body, are known as non essential amino acids.e.g. Glycine ,
Alanine (R=CH3)On the other hand, those which cannot be synthesised in the body and must be obtained through
diet, are known as essential amino acids.e.g. Phenylalanine.
12. Zwitter ion: In aqueous solution, the carboxyl group can lose a proton and amino group can accept a proton,
giving rise to a dipolar ion known as zwitter ion.
13. Peptide bond or Peptide linkage. Chemically, peptide linkage is an amide formed between –COOH group and
–NH2 group. peptide bond –CO–NH– Involves of elimination of a water.
14. ‘When the number of such amino acids is more than ten, then the products are called polypeptides.
15. Primary structure of proteins: It tells us sequence of ά-amino acids present in the polypeptide chains. Each
protein has a specific sequence of ά-amino acids.
16. Secondary structure of proteins:It refers to shape in which long polypeptide chain exists.A protein may
assume α-helix and β-pleated sheet structure.
17. α-Helix results due to regular coiling of polypeptide chain which is stablised by intramolecular hydrogen
bonding.e.g.Keratin
18. In β-structure all peptide chains are stretched out to nearly maximum extension and then laid side by side
which are held together by intermolecular hydrogen bonds.e.g Silk
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19. Tertiary structure of proteins: The tertiary structure of proteins represents overall folding of the polypeptide
chains i.e., further folding of the secondary structure. The main forces which stabilise the 2° and 3° structures of
proteins are hydrogen bonds, disulphide linkages, van der Waals and electrostatic forces of attraction.
20. Globular proteins : This structure results when the chains of polypeptides coil around to give a spherical
shape.They are soluble in water.e.g. Insulin and albumins
21. Fibrous proteins: The molecules have long and thread like structures. They are insoluble in water. examples are
keratin (present in hair, wool, silk)
22. Quaternary structure of proteins: Some of the proteins are composed of two or more polypeptide chains
referred to as sub-units. The spatial arrangement of these subunits with respect to each other is known as
quaternary structure
23. Denaturation of Proteins: When a protein in its native form, is subjected to physical change like change in
temperature or chemical change like change in pH, the hydrogen bonds are disturbed. This is called denaturation of
protein. During denaturation 2° and 3° structures are destroyed but 1º structure remains intact. Examples :
coagulation of egg white on boiling, curdling of milk
24. Nucleic acids : The particles in nucleus of the cell, responsible for heredity, are called chromosomes which are
made up of proteins and another type of biomolecules called nucleic acids.
25. Nucleosides: It consists of nitrogen containing bases and four carbon sugar. Base + Sugar → Nucleosides
26. Nucleotides: It consists of nitrogen containing bases ,four carbon sugar and phosphate unit.
Base + Sugar + Phosphate → Nucleotides.
27. RNA molecules are of three types and they perform different functions. They are named as messengerRNA (m-
RNA), ribosomal RNA (r-RNA) and transfer RNA (t-RNA).
28. DNA & RNA
DNA RNA
It contains β-D-2-deoxyribose sugar. It Contains β-D-ribose sugar.
It Contains adenine (A), guanine (G), It Contains adenine (A), guanine (G),
cytosine (C) and thymine (T) as bases. cytosine (C), uracil (U). as bases
It has double helix structure It has single helix structure
It Can replicate It Can not replicate
It is present in the nucleus cell. It is present in the cytoplasm of the cell.
(QUESTIONS RELATED TO CARBOHYDRATES)
1. Define carbohydrates.
2. How are carbohydrates classified on the basis of their behaviour on hydrolysis?
3. What are reducing and non reducing sugars? Give example of each.
4. How is Glucose prepared? Write the reactions when D-Glucose reacts with following: (a)Hydrocyanicacid, HCN (b)
acetic anhydride (c) Tollens reagent (d)HI (e)ConcHNO3 (f)Phenyl Hydrazine (g) Hydroxlamime (h)Bromine
5. Write the reaction which show that all the carbon atoms in glucose are linked in a straight chain.
6. How do you explain the presence of an aldehydic group in a glucose molecule?
7. How do you explain the presence of five —OH groups in glucose molecule?
8. Under what conditions glucose is converted to gluconic and saccharic acid?
9. Explain Pyranose structure of glucose.
10. Write such reactions & facts of Glucose which cannot be explained by its open chain structure.
11. Define the term Anomers.
12. What is essentially the difference between the α- form of glucose & β- form of glucose?
13. Explain the structure of Structure of Fructose
14. What is the basic structural difference Glucose and Fructose?
15. Despite having an aldehyde group glucose does not give 2, 4 - DNP test. What does this indicate?
16. What is the significance of D and (+) in D(+)-glucose ?
17. Classify the following into monosaccharides and disaccharides.Ribose,2 deoxyribose, maltose, galactose, fructose
and lactose.
18. Monosaccharides contain carbonyl group hence are classified, as aldose or ketose. The number of carbon atoms
present in the monosaccharide molecule are also considered for classification. In which class of monosaccharide
will you place fructose?
19. What are the hydrolysis products of (a) Sucrose. (b) Lactose (c)Maltose.
20. Name the sugar present in milk. How many monosaccharide units are present in it? What are such oligosaccharides
called?
21. Glucose or sucrose are soluble in water but cyclohexane or benzene are insoluble in water. Explain
22. How do you explain the absence of aldehyde group in the pentaacetate of D-glucose?
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23. Write two main functions of carbohydrates in plants.
24. What do you understand by the term glycosidic linkage?
25. Name the linkage connecting monosaccharide units in polysaccharides.
QUESTIONS RELATED TO PROTEINS
1. Draw the structure of Glycine, Alanine, and Phenylalanine.
2. Amino acids may be acidic ,alkaline or neutral.How does this happen.
3. ●What are essential and non essential amino acids? Give two examples of each type.
4. ●Write a note on zwitter ion and isoelectric point.
5. Amino acids behave like salts rather than simple amines or carboxylic acids. Explain
6. What do you understand by the term Peptide linkage&Poly Peptide linkage?
7. Write the name of linkage joining two amino acids.
8. ●Distinguish between the following: (a)Essential &Nonessential amino acids (b) Fibrous &Globular proteins(c)
-helix and -pleated sheet proteins
9. Write a note on: (a)Primary structure of proteins (b) secondary structure of proteins
10. What are the common types of secondary structure of proteins?
11. ●What type of bonding helps in stabilizing the -helix structure of proteins
12. ●How do you explain the amphoteric behaviour of amino acids?
13. What is Denaturation of proteins
14. ●What is the biological effect of Denaturation on the structure of proteins?
15. Where does the water present in the egg go after boiling the egg.
16. Coagulation of egg white on boiling is an example of denaturation of protein. Explain it in terms of structural
changes.
17. The melting point and solubility in water of amino acids are generally higher than that of the corresponding
haloacids.Explain.
18. Where does the water present in the egg go after boiling the egg?
19. What changes occur in the nature of egg proteins on boiling?
20. Name the type of bonding which stabilizes -helix structure of proteins.
21. Name the type of bonding which stabilizes -pleated sheet proteins .
22. Name the type of bonding which stabilizes tertiary structure of proteins.
QUESTIONS RELATED TO NUCLEIC ACIDS
1. Define Nucleic acids. How are they classified? Mention their two important sources.
2. Write the full forms of DNA and RNA.
3. Write the important differences between DNA and RNA.
4. Name the four bases present in RNA.
5. Of the two bases below which one present in RNA and which one present in DNA? (i) Thymine (ii) Uracil
6. Out of the two bases Thymine & Uracil which one is present in DNA.
7. Out of the four bases name those which are common to both DNA
8. Which of the following are purine bases? Guanine,AdenineThymine & Uracil
9. What is the difference between a nucleoside and a nucleotide?
10. What is phosphodiester linkage.
11. Which moieties of nucleosides are involved in the formation of phosphodiester linkages present in
dinucleotides?
12. The two strands in DNA are not identical but are complementary. Explain
13. What are different types of RNA molecules which perform different functions.?
14. What products would be formed when a nucleotide from DNA containing thymine is hydrolysed?
15. When RNA is hydrolysed, there is no relationship among the quantities of different bases obtained. What does
this fact suggest about the structure of RNA?
QUESTION RELATED TO VITAMIN
1. Define vitamins. How are vitamins classified?
2. Name the deficiency diseases caused due to lack of vitamin A, C, E, B1, B2, B6 , B12 E &K.
3. Give the main sources of vitamin A, C, E, B1, B2,, B6 , B12 E &K.
4. Write the name of Vitamin responsible for the : (a) Pernicious anaemia (b) Increased blood clotting time(c)
Xerophthalmia(d) Rickets (e) Muscular weakness (f) Night blindness (g) Beri Beri(h) Bleeding gums (i) Osteomalacia
5. Which of the following B group vitamins can be stored in our body? Vitamin B1, Vitamin B2 ,Vitamin B6 Vitamin B12
6. Except for vitamin B12, all other vitamins of group B, should be supplied regularly in diet. Why?
7. Why cannot Vitamin C be stored in our body? Why Vitamin B & C essential for us.