CHM330: ULTIMATE GUIDE FOR STUDYING NATURAL PRODUCT

By | October 1, 2019

CHM 330 NATURAL PRODUCT (COURSE OUTLINE)
  • Extraction, purificationand isolation of natural products.
  • Introduction to structural elucidation of natural products.
  • Classification and chemistry of carbohydrates,terpenes, steroids, glycosides, alkaloids, amino acids, proteins and lipids.

MATERIAL ONE : WHAT YOU SHOULD KNOW

PART A

ULTIMATE GUIDE FOR STUDYING NATURAL PRODUCT

 

– Explain briefly the following:
.Disaccharide
. Monosaccharide
.Disaccharide
. Oligosaccharide
. Polysaccharide
-Use mild oxidation to differentiate between teiroses: D-erythrose and D-threose
-Describe the term epimer and illustrate with erythrose and threose
– Q1 (c) Compare the reactions of an aldohexose and a 2-ketohexose with:
.Tollens’ reagent
. Fehling’s solution
. Benedict’s reagent
. Br2H20
– Describe the changes that signal a positive test and give formulas for the reagents in Q1 (c) above
– Classify the product from the aldohexose in QI (c) above
– Predict the products for the reaction of D-mannose with PhNHNH2, show the intermediates, and classify the product
– Predict the steps for the conversion of a D-aldopentose to an aldohexose in the original version of the Kiliani-Fischer method.

-Suggest a reason why oxidation of a-Glucopyranose by HIO4 is more rapid than the B-isomer at the 1.2-bond.
-State spectroscopic evidence available for the determination of structure of
D-glucose
-Account for the isolation of phenolic glycosides from naturally occurring plants
– Outline all the basic steps in the synthesis of a named glycoside.
– illustrates with specific example the basic fused steroid ring system present in many important naturally occurring compounds.
-State one concern that people may have about the addition of extra plant sterols to margarine
-What are steroids?
– State the classes of steroids based on their functions
– Discuss the validity of the following statements:
. Glucose is the only aldose that mutarotates
. Ketoses also mutarotate
. Glycosides mutarotate
. There is a relationship between the ability of a sugar to mutarotate and reduce Fehling’s reagent
– Outline the conversion of arbutin to pentarmethylarbutin
– Mention two natural plant polysaccharides consisting of only D-glucose units
– Write names and structures of two compounds in the classes of amino acids listed below.
.Aliphatic unsubstituted amino acids
.Aliphatic substituted amino acids.
.Diamino acids
.Aromatic amino acids
. How can we test for amino acid in an unknown sample?
– Use suitable equations to illustrate three reactions of amino acids
– List three main process that are involved in isolation of proteins and outline the procedure involved in the process listed in above.

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– Mention four classes of
.Simple proteins
.Conjugated proteins
-Write three examples protein in each of the classes
– State the four main characteristics of alkaloids
– Write structures and one medicinal use of each of the following alkaloids
. Cocaine
.Quinine
. Caffeine
. Nicotine
-Briefly describe the isolation and characterization of alkaloid from a named plant
– Give name and structure of a compound for each of the following classes of alkaloids
. Phenylethylamine
. Indole and pyridine
.Pyrrolidine
.Tropane and quinosalizidine
– Illustrate with suitable equations the chemical synthesis of the following alkaloids
. Papaverine
. Norlaudanosine
. Laudanosine

MATERIAL ONE : WHAT YOU SHOULD KNOW

PART  B

ULTIMATE GUIDE FOR STUDYING NATURAL PRODUCT

– Distinguish between Proteingenic and Non-proteingenic amino acids. Give two examples of each mentioned above.
– Write three names and structures for each of the following classes of amino acids below.
-Aliphatic insubstituted amino acids, Aliphatic substituted amino acids, Diaminoacids and
Aromatic amino acids
– Use suitable equations to explain three chemical reactions of amino acids.
-Explain briefly, the extraction, precipitation and purification of proteins
– Outline the five main characteristics of alkaloids
– Write the structures and medicinal uses of each of the following alkaloids: Cocaine, Quinine,
Caffeine, Nicotine, Morphine and Heroin
– Explain in details, the isolation, purification and structural identification of a named alkaloid.
– Use suitable equations to illustrate the chemical synthesis of the following alkaloids
. Papaverine
. Laudanosine
. Norlaudanosine
– What are lipids?
– 2(b) Based on structure, list two main classes of lipids? The under listed compounds are lipids:
.Oleic acid
. geranyl acetate
. tripalmito glycerides

. decanol, arachidonic acid,
.glycerol
. linoleic acid
. linolenic acid
– 2(c) Assign each of the compounds above to the two main classes of lipids listed in 2(b)
. 2(d) Indicate the compounds that could occur in fixed oil among the compounds listed in 2(c) above
– 2(e) ldentify the compounds that can form the type of compound indicated in 2(d) above
-Use suitable chemical equation to illustrate the formation of the type of compound identified
in 2(e) above
-Which of the compounds identified in 2(e) above determine the physicochemical properties of fixed oil.
– What are Oleo chemicals?
– 3(b) State the type of compound that could form oleo chemicals,
– Give strnucture of the type compound stated in 3(b) above
– 3(c) Signify the functional groups that favour the formation of the oleo chemical from the compound given in 3(c) above
– 4(e)List three oleo chemicals obtainable from the compound given in 3(B) above
– Use suitable chemical equation to illustrate the formation of the oleo chemicals listed in 4(e) above
– State two uses of each of the oleo chemicals given in 4(e)

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MATERIAL ONE : WHAT YOU SHOULD KNOW

PART C

ULTIMATE GUIDE FOR STUDYING NATURAL PRODUCT

– 1(a) Identify the two anomeric carbons and the glycosidic bond in sucralose disaccharide.
-Draw the open chain form of each of the monosaccharides in 1(a) above
-Based on what you know of glycosidase enzyme reactions, predict the products for enzymatic hydrolysis of the glycosidic bond in cellulose.
– State three classes of bicyclic monoterpenoids.
-Give structures and names of two compounds in each of the classes.
– Use suitable chemical equations to show how each of the following transformations can be effected.
.Limonene to a-Terpeneol
. a-Terpenene to Terpene-4-ol
. Mytcene to Linalool
. β-Fernescene to Nerolidol
– Describe briefly, the chemistry of steroids.
– (b.) State the compound that could serve as precursor for the biosynthesis of steroids in the body?
– ( C) Give the structure of the compound mentioned in (b.) above.
-(d) Identify the position of the carbons on which the methyl groups and the long hydrocarbon chain are attached to the compound named in ( C) above.
-Outline briefly, how the compound mentioned in (d). above can be synthesized from a named terpene,
– How can we test for the following metabolites in unknown samples
.Amino acid
. Protein
. Alkaloid
-Outline four classes for each of simple proteins and conjugated protein
-Write two examples of each afore mentioned class.

 

 

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