CARBOHYDRATES,STEREOISOMERISM,IMPORTANT COMPOUNDS,REACTIONS,PROPERTIES and STRUCTURE

BIOCHEMISTRY
WELFREDO LUBRICO YU JR
CEBU TECHNOLOGICAL UNIVERSITY MAIN CAMPUS
MAED TEACHING SCIENCE

1. Carbohydrates: Structure Properties,Classification and Functions IMPORTANT COMPOUNDS,STEREO ISOMERISM AND REACTION Presented and Reported By WELFREDO LUBRICO YU,JR. and ROSCELA MAE D. ARIZO

2. IODINE TEST EXPERIMENT NAME OF FOOD COLOR(IODINE SOLUTION ) CONCLUSION 1. 2. 3. 4. 5. 6. 7.

3. Objectives: Identify the structure,properties of carbohydrates as a biological molecule and Important compounds,stereo isomerism and reaction . Distinguish the Classification Monosaccharide , Disaccharide and Polysaccharide according to their structure and functions and Important compounds,stereo isomerism and reaction . Point out the importance of carbohydrates in our daily activities and Important compounds,stereo isomerism and reaction .

4. What is Carbohydrates? - The empiric formula is (CH 2 O)n, “hydrates of carbon ” CHEMICAL ELEMENTS CARBON , HYDROGEN , OXYGEN

5. What is a MONOMER? It means “ Building Block ”. A molecule that can be bonded to other identical molecules to form a polymer. What is the monomer of CARBOHYDRATES? Saccharides Sugar Glucose (C6H12O6) Energy ( brain cells/ thinking,breathing,moving ) Aids in digestive process,breaking down and digesting fats and proteins

6. LET’S WATCH THE VIDEO OF CARBOHYDRATES…

7. “Eat more and it will turns to FAT” “If we eat more carbohydrates than are needed for energy, the extra is stored in the liver or in the tissues as FAT.

8. What is Saccharides? 3

9. What are the functions of Carbohydrates? Provide energy (most important) Provide bulk in the diet Provide dietary Fiber Assist in the metabolism of fats Spare protein for tissue maintenance

10. What are the forms of Carbohydrates? COMPLEX CARBOHYDRATES( a.k.a.“starches ”) POLYSACCHARIDES (many) e.g., starches,cellulose,fibers SIMPLE CARBOHYDRATES(a.k.a. “sugars”) MONOSACCHARIDES (1) DISACCHARIDES (2)

11. What are some sources of Starch and Sugars? Sources of Sugars Fruits, honey, milk, juices (100% cocktails), alcohol, syrups, cakes, cookies,candies,soda,added to many refined foods. Sources of starch cereals grains( wheat,oats,rice,etc ), pasta,breads,legumes , vegetables,potatoes,anything made with flour

12. Types of Carbohydrates?

13. 2 Carbohydrates C arbohydrates are broadly defined as polyhydroxy as al d ehy d es or ke t one s a n d t h eir derivat i ves or substances that yields one of these compounds Composed of carbon, hydrogen, and oxygen Functional groups present include hydroxyl groups -ose indicates sugar

14. C arbohydrates are the most abundant of all the organic compounds in nature. In plants, energy from the Sun is used to convert carbon dioxide and water into the carbohydrate glucose. Many of the glucose molecules are made into long-chain polymers of starch that store energy. About 65% of the foods in our diet consist of carbohydrates. Each day we utilize carbohydrates in foods such as bread, pasta, potatoes, and rice. Other carbohydrates called disaccharides include sucrose (table sugar) and lactose in milk. During digestion and cellular metabolism, carbohydrates are converted into glucose, which is oxidized further in our cells to provide our bodies with energy and to provide the cells with carbon atoms for building molecules of protein, lipids, and nucleic acids. In plants, a polymer of glucose called cellulose builds the structural framework. Cellulose has other important uses, too. The wood in our furniture, the pages in your notebook, and the cotton in our clothing are made of cellulose.

15. Compiled and Edited by Dr.Syed Ismail,MAU, Parbhani 4 Function of Carbohydrates in Cells Major source of energy for the cell Major structural component of plant cell Immediate energy in the form of GLUCOSE Reserve or stored energy in the form of GLYCOGEN

16. 5 Classification of Carbohydrates Carbohydrates are classified according to the number of subunits that make them up 3 Types of Carbohydrates  Monosaccharides  Oligosaccharides Disaccharides Trisaccharides T etrasa c charides  Polysaccharides

17. 6 Monosaccharides are simple sugars, or the compounds which possess a free aldehyde (CHO) or ketone (C=O) group and two or more hydroxyl (OH) groups. They are the simplest sugars and cannot be hydrolysed further into smaller units. Monosaccharides contain a single carbon chain and are classified on the basis of number of carbon atoms they possess, and as aldoses or ketoses depending upon their groups.

18. 7 Monosaccharides Classification by Carbon Atoms Su gar Struc tur e formula Al d o s es K eto s es 1 . T riose C 3 H 6 O 3 Glyceraldehydes 2 . T etroses C 4 H 8 O 4 D e hyd r oxy acetone Erthrulose 3 . P ento s es C 5 H 10 O 5 Erythrose, Threose Xylose Ribose A r a binose Ribul o s e 4. Hexoses C 6 H 12 O 6 Glucose G a lactose Mannose Fructose

19. Compiled and Edited by Dr.Syed Ismail,MAU, Parbhani 8 D-glucose “dextrose” Blood sugar D-galactose D-fructose “ Levulose ” Fruit sugar Fructose: The sweetest of all sugars – (1.5 X sweeter than sucrose) Occurs naturally in fruits and honey “the fruit sugar” Glu cose Other names: Dextrose and Blood Sugar. A component of each disaccharide . Monosaccharides Hexoses Galac t ose  The essential energy source for all body functions  . Seldom occurs freely in nature  Binds with glucose to form sugar in milk: lactose.  Once absorbed by the body, galactose is converted to glucose to provide energy.

20. Compiled and Edited by Dr.Syed Ismail,MAU, Parbhani 9 Steriochemistry Optical isomers (= enantiomers) differ from each other in the disposition of the various atoms or groups of atoms in space around the asymmetric carbon atom. These are, in fact, the mirror image of each other. These may also be likened to left- and right-handed gloves. One form in which H atom at carbon 2 is projected to the left side and OH group to the right is designated as D-form and the other form where H atom is projected to the right side and OH group to the left is called as L-form (note the use of small capital letters D and L) For example, the glyceraldehyde has only one asymmetric carbon atom (numbered as 2) and it can, therefore, exist in 2 isomeric forms :

21. D-Aldoses containing three , four , five and six atoms 10

22. 11 Properties of monosaccharides Mutarotation : when a monosaccharide is dissolved in water, the optical rotatory power of the solution gradually changes until it reaches a constant value. For ex : when D- glucose is dissolved in water, a specific rotation of +112.2 o is obtained, but this slowly changes , so that at 24h the value has become +52.7 o . This gradual change in specific rotation is known as mutarotation. This phenomenon is shown by number of pentoses, hexoses and reducing disaccharides. Glucoside formation : when D-glucose solution is treated with methanol and HCl, two compounds are formed, these are α – and β-D- glucosides. Thus, formed glucosides are not reducing sugar and also doesnot show phenomenon of mutarotation Reducing power : Sugars having free or potentially free aldehyde or ketone group have an ability to reduce the cupric copper to cuprous oxidized + 2Cu + Reducing sugar + 2 Cu ++  (cupric) sugar (cuprous) Oxidation / Reduction: The alcoholic OH, aldehyde (COH) or keto (C=O) group are oxidized to carboxyl group with certain oxidizing agents. The oxidation may be brought under mild or with vigorous oxidizing condition With mild oxidant like BrH 2 O : In this group only aldehyde is oxidized to produce gluconic acid (monocarbonic). Ketoses do not respond to this reaction.

23. 12 With strong Oxidizing agent like Conc HNO 3 : Both aldehyde or ketone groups are oxidized to yield dicarboxylic acids Oxidation with metal hydroxides: Metal hydroxides like Cu(OH)2, Ag OH oxidize free aldehyde or ketone group of mutarotating sugar and reduce themselves to lower oxides of free metals Reduction: The aldehyde or ketone group present can be reduced to its respective alcohol with sodium amalgum. For ex: Fructose and glucose give the hexahydric alcohol i.e. Sorbitol and Mannitol Dehydration : The monosaccharides when treated with Conc H 2 SO 4 , it get dehydrated to from 5 – hydroxyl – methyl furfural derivative Methylation or Esterification : The glucosidic and alcoholic OH group of mono saccharides and reducing disaccharides react with acetylating agent like acetic anhydride in pyridine to from acetate derivatives called esters.

24. C arbohydrates with free carbonyl groups or in hemiacetal form give positive tests to Benedict’s and Fehling’s reagents without having been hydrolyzed are referred as ‘reducing’ sugars ; others ( i . e ., the acetal types) are then ‘non-reducing’ sugars

25. Oligosaccharides These are compound sugars that yield 2 to 10 molecules of the same or different monosaccharides on hydrolysis. Accordingly, an oligosaccharide yielding 2 molecules of monosaccharide on hydrolysis is designated as a disaccharide, and the one yielding 3 molecules of monosaccharide as a trisaccharide and so on. Disaccharides – Sucrose, Lactose, Maltose, Cellobiose, Trehalose, Gentiobiose, Melibiose Trisaccharides – Rhamninose, Gentianose, Raffinose (= Melitose), Rabinose, Melezitose Tetrasaccharides – Stachyose, Scorodose Pentasaccharide – Verbascose The molecular composition of the 3 legume oligosaccharides (viz., raffinose, stachyose and verbascose) is shown below : α-Galactose (1–6) α-Glucose (1–2) β-Fructose Raffinose α-Galactose (1–6) α-Galactose (1–6) α-Glucose (1–2) β-Fructose Stachyose α-Galactose (1–6) α-Galactose (1–6) α-Galactose (1–6) α-Glucose (1–2) β-Fructose Verbascose

26. 15 Disaccharides Composed of 2 monosaccharides cells can make disaccharides by joining two monosaccharides by biosynthesis. Glucose + fructose = sucrose Table sugar Found naturally in plants: sugar cane, sugar beets, honey, maple syrup Sucrose may be purified from plant sources into Brown, White and Powdered Sugars. Glucose + galactose = lactose The primary sugar in milk and milk products. Many people have problems digesting large amounts of lactose (lactose intolerance) Glucose + glucose = Maltose Produced when starch breaks down. Used naturally in fermentation reactions of alcohol and beer manufacturing.

27. 16 Trisaccharides: Composed of three monosaccharide ex: Raffinose (Formed by one mole of each i.e. glu, fruc, galac) Tetrasaccharides : ex: Stachyose (composed of two moles of galactose one mole of glu & one mole of fruct)

28. Compiled and Edited by Dr.Syed Ismail,MAU, Parbhani 17 Polysaccharides C ontaining 10 or more monosaccharide units attached together Examples Starch- digestible Glycogen- digestible Fiber- indigestible Long chains of glucose units form these polysaccharides Cellulose gives structure to plants, fiber to our diet Glycogen is an energy storage sugar produced by animals Liver cells synthesize glycogen after a meal to maintain blood glucose levels

29. homopolysaccharides , which yield, on hydrolysis, a single monosaccharide and heteropolysaccharides ,which produce a mixture of monosaccharides on hydrolysis. Based on their functional aspect, the polysaccharides may be grouped under two heads : Nutrient (or digestible ) polysaccharides. These act as metabolic reserve of monosaccharides in plants and animals, e.g ., starch, glycogen and inulin. Structural (or indigestible ) polysaccharides. These serve as rigid mechanical structures in plants and animals, e.g .,cellulose, pectin and chitin and also hyaluronic acid and chondroitin . A great majority of carbohydrates of nature occur as polysaccharides C hemically , the polysaccharides may be distinguished into

30. 19 Types of Polysaccharides 1. Starch The major digestible polysaccharide in our diet. The storage form of carbohydrate in plants. Sources: Wheat, rice, corn, rye, barley, potatoes, tubers, yams, etc. Two types of plant starch: Amylose Amylopectin

31. 20 Amylose : is in the form of straight chain linked together with α- 1-4, linkages indicating 300 – 5,500 glucose units per molecules, molecular wt range from 10 5 to 10 6 . Generally it is water soluble and gives blue colour with iodine. Amylopectins : It contain beside straight chain several branched chains, which are arranged in α—1-4 and β-1-6 linkage units, one molecule of amylopectin contains 50,000 to 5,00,000 glucose molecules, molecular wt. range from 10 7 to 10 8 , it is insoluble in water and gives purple colour with iodine .

32. Compiled and Edited by Dr.Syed Ismail, MAU, Parbhani 21 Types of Polysaccharides 2. Cellulose - form cell walls in plant cells also called fiber or ruffage indigestible by humans

33. 22 Types of Polysaccharides 3. Glycogen The storage form of glucose in the body. Stored in the liver and muscles. Found in tiny amounts in meat sources. Not found in plants. Not a significant food source of carbohydrate.

34. Glucose is the most important energy source of carbohydrates to the mammals (except ruminants). The bulk of dietary carbohydrate (starch) is digested and finally absorbed as glucose into the body. Dextrose (glucose in solution in dextrorotatory form) is frequently used in medical practice. Fructose is abundantly found in the semen which is utilized by the sperms for energy. Several diseases are associated with carbohydrate's e.g., diabetes mellitus, glycogen storage diseases galactosemia. Accumulation of sorbitol and dulcitol in the tissues may cause certain pathological conditions e.g. cataract, nephropathy. The non-digestible carbohydrate cellulose plays a significant role in human nutrition. These include decreasing the intestinal absorption of glucose and cholesterol, and increasing bulk of feces to avoid constipation. The mucopolysaccharide hyaluronic acid serves as lubricant and shock absorbent in joints. The mucopolysaccharide heparin is an anticoagulant( prevents blood clotting). The survival of Antarctic fish below -2 o C is attributed to the antifreeze glycoproteins. streptomycin is a glycoside employed in the treatment of tuberculosis Some clinical concepts

35. What are monosaccharide? Glucose (C6H12O6 )-Simplest form of sugar called DEXTROSE. GREEK WORD “SWEET” meaning blood “SUGAR”. FRUCTOSE (C6H12O6 )- FRUIT SUGAR GALACTOSE (C6H12O6 )- MILK SUGAR

36. What are Disaccharide? Molecular Formula: C 12 H 22 O 11 Lactose

37. Sucrose ( saccharose ) glucose + fructose Sucrose is  t able sugar. It is purified from sugar cane or sugar beets. Maltose glucose + glucose Maltose is a sugar found in some cereals and candies. It is a product of starch digestions and may be purified from barley and other grains. Lactose galactose + glucose Lactose is a disaccharide found in milk. It has the formula C 12 H 22 O 11  and is  an isomer of sucrose. What are Disaccharide? ( Continued)

38. Source: https://www.google.com.ph/ search?tbm = isch&sa =1&ei=nPeAXPmTGLeMr7wPsJ650Ac&q= milo+is+an+example+of+maltose&oq = milo+is+an+example+of+maltose&gs_l =img.3...434715.462463..462760...0.0..0.187.4323.26j14......0....1..gws-wiz-img.....0..0i67j0j0i8i30j0i30j0i24.mhLUGa-Ch_Y#imgrc=tI8yFrk00LnuFM:

39. What are Polysaccharide?

40. What are Polysaccharide? Continued

41. What are Polysaccharide? Continued

42. What are Polysaccharide? Continued

43. What are Polysaccharide? Continued

44. What are their Characteristics? SIMPLE CARBOHYDRATES(a.k.a. “sugars”) Water soluble Occur in “ fruits,milk,honey ” Occur as refined sugars and syrups COMPLEX CARBOHYDRATES(a.k.a. “starches”) Insoluble Found in plants,seeds , roots and tubers.

45. What is Dietary Fiber? Dietary fiber (a.k.a. “Fiber”) Soluble and Insoluble Indigestibe,provide no calories,found in plant products Sources: vegetables,Whole Grains,Fruits,Bran,Flax,Legumes .

46. IMPORTANT COMPOUNDS NUCLEIC ACID -macromolecules whose function is the storage and transfer of genetic information.Without NA,enzymes which direct chemical reactions in the cell,and protein,annot be made in the living cell. RNA PROTEINS DNA

47. 1.DNA TO DNA DUPLICATION 2.DNA TO RNA TRANSCRIPTION 3.RNA TO PROTEINS TRANSLATION TWO TYPES OF NUCLEIC ACID 1.DNA (genetic material of cell example BLUEPRINT) 2.RNA(RESPONSIBLE FOR PROTEIN SYSNTHESIS) NUCLEC ACIDS ARE POLYNUCLEOTIDES=PHOSPHATE ESTER OF A NUCLEOSIDE.A NUCLEOSIDE CONSISTS OF A BASE AND A SUGAR. MADE UP OF THE SAME THINGS : BASE,SUGAR,AND PHOSPHATE COMPONENTS OF NUCLEOTIDES : PURINE BASES,PYRIMIDINE BASES,SUGARS,PHOSPHORIC GROUP,BASE-PAIRS IN DNA,BASE PAIRS IN RNA,NUCLEOSIDE HYDROLYSIS OF RNA MAY RESULT TO POLYNUCLEOTIDES,MONONUCLEOTIDES,PURINES AND PYRIMIDINE BASES,SUGAR AND PHOSPHATES.

48. PROTEINS -Main constituent of living cells.They are made of C,H,O,N (example :96 %OUR BODY WEIGHT and 4 % Ca,P,K,S,Na,Cl,Mg and Trace elements for life)and usually have sulfur and have molecular weights between 10,000 to million or more. - Polymers of amino acid linked together by peptide bonds - Enzyme s is also called as proteins that catalyze or fasten out the reaction (example: SNAKE WHEN THEY EAT) - Hormones –chemical messengerr,the growth hormones - Antibodies fight foreign bacteria forming PHAGOCYTES - Membrane transport proteins –pathways goes outside or inside the cell.Assist the molecules inside or outside the cell. - Motile proteins (movement proteins Example is SPERM that is made of protein flagella) - Receptor Proteins -Cell to cell recognition - Regulatory Proteins – controls many cellular regulatory proteins (example ENZYME because they regulate) - Storage protein -sources of amino acid,example egg white and In the human placenta -Structural proteins-structure of proteins,example the microfilament,microtubules,collagen in skin

49. IMPORTANT COMPOUNDS LIPIDS -Insoluble in water -soluble to chloroform/alcohol -fats are subgroups of lipids,composed of glycerol and fatty acids called triglycerides -major source of energy that can be converted ito sugar /glycogen . -SATURATED (animals-HDL) VS UNSATURATED(vegetables-LDL) FATS

50. IMPORTANT COMPOUNDS LIPIDS (EMULSIFICATION –digestion of fats,breaking of big fats into smaller fat droplets that can be absorb in our body) -ASTHEROSTEROSIS-cardiovascular disease that flow of blood is trap and causes cardiac arrest. -Why most of the male has no (bil2x)? It is because male works faster than female so that the fats surrounding in organs act as CUSHIONS that absorbs/protect muscle part. -TYPES:FATS,PHOSPHOLIPIDS(parts of cell membrane),SPHINGOLIPIDS (LOCATED IN MANY MAMMALS-adhesion site),WAXES (COATING AGENT),STEROIDS (cholesterol ,hormones and sex hormonses ).LDL for sex hormones while HDL for cholesterol -Cholesterol is the processor of molecule/VITAMIN D. “ WE NEED SUNLIGHT TO CONVERT FATS INTO VITAMIN D”

51. REACTIONS OF CARBOHYDRATES

52. G l u c o s e Bromine water G lu c on i c acid Glu c ose Con . H NO3 (nitric acid) Glu c aric acid +H2O O XI D A TION SPECIFIC FOR ALDOSE MIL D S T R ONG

53. 1 2 4 5 5 reactions Reduction 3

54. Reduction of Monosaccharide  C=O of aldoses or ketoses can be reduced to C- OH by NaBH4 ( sodiumtetrahyridoborate (III)  Name the sugar alcohol by adding – itol to the root name of the sugar; commonly known as an alditol.  Reduction of D-glucose produces D-glucitol, commonly called D-sorbitol.  Reduction of D-fructose produces a mixture of D- glucitol and D-mannitol.

55. Glucose + sodium amalgam = sorbitol Fructose + sodium amalgam = sorbitol and mannitol Glucose/fructose + HI/ Red phosphorus = n – hexane (prolonger heating with con. Hydroic acid and red phosphorus )

56. Glucose /fructose + hydrogen cyanide = g l ucose cyanohydrid / fructose cyanohydrin Glucose/ fructose + hydroxyl amine = glucose amine / fructose amine +water

57. Glucose/ fructose + phenyl hydrazine (condenses) Glucose/ fructose phenylhydrazone (warmed with excess phenyl hydrazine) Glucosazone /fructosazone

58. Reducing action Oxidation by Tollens Reagent Sugars that reduce Tollensreagent are called Reducing sugars Tollens reagent – ammoniacal silvar nitrate solution Silvar mirror test Metallic silver formation Glucose gives gluconic acid + metallic silver Fructose gives glycollic acid +trihydroxy butyric acid+glycollic acid + metallic silver

59. Acetylation glucose / fructose + acetic anhydride glucose /fructose pentaacetate + acetic acid Methylation Glucose / fructose + penta methyl glucose (In presence of DRY HCl) Methyl fructoside /methyl glucoside + H2O

60. Glucose / fructose Dimethyl su l p h a t e In presence of alkali

61. pe n t am e t h yl fructose pe n t am e t h yl glucose

62. Enediol Rearrangement In base, the position of the C=O can shift Aldose ketose Chemists use acidic or neutral solutions of sugars to preserve their identity.

63. Epimerization

64. Proton alpha to carbonyl group (in aldehyde or ketone) is reversibly removed; form an enolate-C2 no longer chiral. Reprotonation can occur on either side of the enolate to give configuration products

65. Ester Formation Acetic anhydride with pyridine catalyst converts to acetate esters. Eg . Glucose +acetic anhydride+phosphoric acid Glucose 1 pho s ph a t e

66. Aldoses& ketoses are converted to acetals by treatment with alcohol in the presence of acid Aldose /ketose +ammonia = glycosylamine Al d ose k e t ose Acid Bas e F orms Ace t als

67. Ether Formation Convert all -OH groups to -OR, using a Williamson synthesis, after converting sugar to acetal

68. Ruff Degradation Aldose chain is shortened by oxidizing the aldehyde to -COOH, then decarboxylation

69. Kiliani-Fischer Synthesis This process lengthens the aldose chain

70. Suc r ose sucrose 200 degree c Losswater caramel Brown amorphus mass Sugar charcol Strong heating

71. Inversion of cane sugar hydrolysis Sucrose invertase glucose + fructose

72. Sucrosate formation Sucrose + Ca hydroxide Ba hydroxide Sr hydroxide Respective sucrosate formation with water

73. sucrose Con. HNO3 O XALIC ACID + W A TE R SUCROSE CON. HCl Laevulinic acid suc r ose O c t a c e t y l sucrose A c e tic acid oxidation Acetyl a ti on

74. Dehydration Sucrose con. H2SO4 C O2 C H 2O SO2

75. METHYLATION SUCROSE + DIMETHYL SULPHATE = OCTAMETHYL SUCROSE +SULPHURIC ACID IN PRESENCE OF ALKALI FERMEN T A TI O N SUCROSE+ H2O GLUCOSE + FRUCTOSE ETHANOL+ CO2

76. NO REACTION WITH Tollens reagent Fehlings Benedicts Phenyl hydrazine Hydroxyl amine Non reducing sugar

77. Starch Action of heat 200- 250 Cleavage of polymer Dextrin (a polysccharide of lower molecular weight ) Iodine test shows a deep blue colour with starch

78. Hydrolysis On boiling with dil. Acid , starch become dextrin then ultimately yield glucose , yield Starch hydrolysed by enzyme diastase maltose

79. Hydrolysis SUCROSE + H2O-----GLUCOSE + FRUCTOSE (SEPARATION OF DISSACHARIDE AND MONOSACCHARIDE) DEHYDRATION SYNTHESIS GLUCOSE+FRUCTOSE---SUCROSE + WATER (FORMATION OF DISSACHARIDE BY MEANS OF REMOVAL OF WATER)

80. Cellulose Hydrolysed with acid to yield glucose

81. Nit r a tion MONO NITRATE DI NITRITE TRI NITRITE MANUFACTURE PLASTICS , PHOTOGRAPHIC FILM GUN COTTON ,EXPLOSIVE

82. ACETYLATION ACETIC ANHYDRIDE , GLACIAL ACETIC ACID ,SULPHURIC ACID DI AND TRI ACETATES SYNTHETIC FIBRES PAINTS AND VARNISHES

83. Colour reactions

84. Molischs test It is indicative of carbohydrate Furfural / hydroxy furfural formed by the action H2SO4 Condenses to form violet ring with alpha naphthanol

85. Barfoeds test Acetic acid + cupric acetate –barfoeds solution Monosaccharides test Cuprous oxide makes red ppt.

86. Benedicts test Benedicts solution – CuSO4 + sodium carbonate + sodium citrate +H2O Reducing sugar Red ppt of cuprous oxide , depending on con.

87. Fehling's Test Fehling's solution –( CuSO4 +CON. H2SO4+H20)+ SODIUM POTASSIUM TARTARATE + NaOH ) For reducing testing Red ppt of cuprous oxide Glucose gives gluconic acid +cuprous oxide Fructose gives trihydroxy butyric acid+ glycollic acid +cuprous oxide

88. Bials test Bials reagent – ferric chloride hexahydrate +con. HCl + orcinol Distinguish b/w pentose and hexose Furfural formation Furfural + orcinol + ferric iron = coloured product Pentose – green Hexose - muddy brown

89. Seliwanoff test For ketoses Reagent – HCl + resorcinol Ketose + HCl =furfural derivative + recorcinol= deep red colour •

90. Diphenylamine test Reagent – H2SO4 , DIPHENYL AMINE,GLACIAL ACETIC ACID ADD TO TEST SOLUTION BOIL 10’ 2 D E O XY SUGAR BLUE / GREEN COLOUR

91. Schiff test ALDOSE + SCHIFFS = MAGENTA COLOUR

92. Anthrone method Furfural formation by H2SO4 Naphthanol form blue colour show prescence of carbohydrate

93. Stereoisomerism

94. STRUCTURAL ISOMERISM GEOMETRICAL ISOMERISM Occurs due to the restricted rotation of C=C double bonds... two forms… CIS and TRANS OPTICAL ISOMERISM CHAIN ISOMERISM Same molecular formula but different structural formulae Occurs when molecules have a chiral centre. Get two non- superimposable mirror images. STEREOISOMERISM Same molecular formula but atoms occupy different positions in space. POSITION ISOMERISM FUNCTIONAL GROUP ISOMERISM

95. Geometric isomers

96. In alkenes CIS Groups/atoms are on the SAME SI DE of the double bond TRANS Groups/atoms are on OPPOSITE SIDES across the double bond

97. RESTRICTED ROTATION OF C=C BONDS Single covalent bonds can easily rotate . What appears to be a different structure is not. It looks like it but, due to the way structures are written out, they are the same. ALL THESE STRUCTURES ARE THE SAME BECAUSE C-C BONDS HAVE ‘FREE’ ROTATION

98. RESTRICTED ROTATION OF C=C BONDS C=C bonds have restricted rotation so the groups on either end of the bond are ‘frozen’ in one position; it isn’t easy to flip between the two. This produces two possibilities . The two structures cannot interchange easily so the atoms in the two molecules occupy different positions in space .

99. cis tra ns cis tra ns

100. Isomerism Constitutional Isomers: Same atoms but linked (bonded) together differently. Spatial orientation not important. 3-methylpentane h e x a n e cyclohexane Are these constitutional isomers of cis but-2-ene? Not this one! It is 2-butene. Cis / trans does not matter.

101. Stereoisomerism Stereoisomers : Same molecular formulae, same connectivity; same constitutional isomer. Different spatial orientation of the bonds. Are these stereoisomers of cis but-2-ene? How does the connectivity differ between these two?

102. Enantiomers and Diastereomers Two kinds of Stereoisomers Enantiomers : stereoisomers which are mirror objects of each other. Enantiomers are different objects, not superimposable. Diastereomers : stereoisomers which are not mirror objects of each other. If a molecule has one or more tetrahedral carbons having four different substituents then enantiomers will occur. If there are two or more such carbons then diastereomers may also occur.

103. Isomers, contain same atoms, same formula Constitutional isomers, different connectivities, bonding. Stereoisomers, same connectivity, different three dimensional orientation of bonds Enantiomers, mirror objects Diastereomers, not mirror objects Summary of Isomerism Concepts

104. Mirror Ob j ects – Carbon with 4 di f fe r ent substituen t s. W e These are m differently ? irror o ? Can We can superimpose two atoms. but not all four atoms. expect enantiomers (mirror objects). Reflect! The mirror plane still relates the two structures. Notice that we can characterize or name the molecules by putting the blue in the back, drawing a circle from purple, to red, to green. Clockwise on the right and counterclockwise on the left. Arbitrarily call them R and S. R S Arrange both structures with the light blue atoms towards the rear…. Notice how the reflection is done, straight through the mirror!

105. Recap: Tetrahedral Carbon with four D i f ferent Substituents. Enantiom e rs Simple Rotation, Sa me Simple Rotation, Sa me Mirror objects. Different, not su p er i mp o sa b l e . E n a n tiom e rs

106. But the reflection might have been done differently. Position the mirror differently…. Reflection can give any of the following… mirror object? All three of these structures are the same, just made by different mirrors. The structures are superimposable. What rotations of the whole molecules are needed to superimpose the structures?

107. Now Superimposable mirror objects : Tetrahedral Carbon with at least two identical substituents . Reflection can interchange the two red substituents. Clearly interchanging the two reds leads to the same structure, superimposable ! Remember it does not make any difference where the mirror is held for the reflection. This molecule does not have an enantiomer; the mirror object is superimposable on the original, the same object.

108. Polarized light vibrates in one plane only, in contrast to ordinary light, which vibrates in all planes. What causes such a rotation of the plane of polarized liight? According to the van’t Hoff theory, such an effect on the plane polarized light is due to the presence of one or more chiral carbon atoms.

109. Fischer projection  A two-dimensional method of indicating the structure of an enantiomer.  Horizontal lines indicate bonds extending forward from the paper and the vertical lines indicate bonds extending backward from the paper.  The formulas are always written with the aldehyde(or ketone) group)-the most highly oxidized-at the top. C HO H C O H CH 2 OH H O H C H O CH 2 OH convert to a Fischer projection

110. Gl y ce r aldeh y de (an aldotriose) O H C H C OH CH 2 OH D (+) O H C HO C H CH 2 OH L (-)

111. References https://chem.libretexts.org/Courses/Sacramento_City_College/SCC%3A_Chem_309_-_General%2C_Organic_and_Biochemistry_(Bennett)/Chapters/14%3A_Carbohydrates/14.2%3A_Classes_of_Monosaccharides   https://www.thoughtco.com/list-of-disaccharide-examples-603876 https://www.google.com.ph/search?q=types+disaccharide+structure&source=lnms&tbm=isch&sa=X&ved=0ahUKEwiByOW9r-vgAhWDA4gKHbvdCKAQ_AUIDigB&biw=1366&bih=608#imgrc=rbgoULCPWd5tuM:   https://www.google.com.ph/search?q=chitin+polysaccharide+function&source=lnms&tbm=isch&sa=X&ved=0ahUKEwiIhYvutevgAhWEP3AKHfPaD_wQ_AUIDigB&biw=1366&bih=608#imgrc=TE6XqhjCaw6pKM: http:// www.softschools.com/quizzes/chemistry/carbohydrates/quiz2006.html https://www.google.com.ph/ search?tbm = isch&sa =1&ei=nPeAXPmTGLeMr7wPsJ650Ac&q= milo+is+an+example+of+maltose&oq = milo+is+an+example+of+maltose&gs_l =img.3...434715.462463..462760...0.0..0.187.4323.26j14......0....1..gws-wiz-img.....0..0i67j0j0i8i30j0i30j0i24.mhLUGa-Ch_Y#imgrc=tI8yFrk00LnuFM : https:// www.youtube.com/watch?v=LeOUIXbFyqk https://www.youtube.com/watch?v=HpywYawQKLk https://www.google.com.ph/search?q=difference+between+carbs+and+carbohydrates&tbm=isch&source=iu&ictx=1&fir=6r8cbSzVKHzzeM%253A%252CO5lbETyrgWDcQM%252C_&vet=1&usg=AI4_-kS8-0RSOjsIroaaNpJo8CFdAOhZNw&sa=X&ved=2ahUKEwiato-J9e_gAhXJc3AKHYY-Ae8Q9QEwAHoECAYQBg#imgrc=6r8cbSzVKHzzeM: https:// www.google.com.ph/search?q=monomer+meaning&oq=monomer+me&aqs=chrome.0.0j69i57j0l4.6402j1j7&sourceid=chrome&ie=UTF-8 https://slideplayer.com/slide/12380414/

112. Further readings Jain, J.L. (2005) Fundamentals of Biochemistry, S. Chand & Company Ltd. Ram nagar, New Delhi, India Karen C. Timberlake (2012) Chemistry : An Introduction to General, Organic, and Biological Chemistry -11th ed. Publishing as Prentice Hall in the United States of America. Satyanarayana, U. (2007) Biochemistry , Books and Allied (P) Ltd, Kolkata, India