Concept explainers
a) Cholesterol, C27H46O
Interpretation:
The degree of unsaturation in cholesterol, C27H46O, is to be calculated.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of
To calculate:
The degree of unsaturation in cholesterol with molecular formula C27H46O.
Answer to Problem 67AP
The degree of unsaturation in cholesterol with molecular formula C27H46O is 5.
Explanation of Solution
Molecular formula of cholesterol is C27H46O. If oxygens are ignored the formula becomes C27H46. A hydrocarbon with twenty seven carbons will have the molecular formula C27H56. The compound given has five pairs of hydrogens (H56-H46=10) less. So its degree of unsaturation is 5.
The degree of unsaturation in cholesterol with molecular formula C27H46O is 5.
b) DDT, C14H9Cl5
Interpretation:
The degree of unsaturation in DDT, C14H9Cl5 is to be calculated and to draw five possible structures with this formula.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of alkanes is CnH2n+2. Knowing this relationship and by working backward the degree of unsaturation in a molecule can be calculated. Each ring or a double bond in a molecule corresponds to a loss of two hydrogens from the formula of alkane. If the compound contains halogens, oxygen and/or nitrogen, then the number of halogens is to be added to the number of hydrogens, the number of oxygens to be ignored and number of the nitrogens is to be subtracted, in arriving at an equivalent hydrocarbon formula.
To calculate:
The degree of unsaturation in DDT with molecular formula C14H9Cl5.
Answer to Problem 67AP
The degree of unsaturation in DDT with molecular formula C14H9Cl5 is 8.
Explanation of Solution
Molecular formula of DDT is C14H9Cl5. Adding five hydrogens for five chlorines, we get the formula as C14H14. A hydrocarbon with fourteen carbons will have the molecular formula C14H30. The compound given has eight pairs of hydrogens (H30-H14=16) less. So its degree of unsaturation is 8.
The degree of unsaturation in DDTwith molecular formula C14H9Cl5 is 8.
c) Prostaglandin E1, C20H34O5
Interpretation:
The degree of unsaturation in prostaglandin E1, C20H34O5 is to be calculated.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of alkanes is CnH2n+2. Knowing this relationship and by working backward the degree of unsaturation in a molecule can be calculated. Each ring or a double bond in a molecule corresponds to a loss of two hydrogens from the formula of alkane. If the compound contains halogens, oxygen and/or nitrogen, then the number of halogens is to be added to the number of hydrogens, the number of oxygens to be ignored and number of the nitrogens is to be subtracted, in arriving at an equivalent hydrocarbon formula.
To calculate:
The degree of unsaturation in prostaglandin E1 with molecular formula C20H34O5.
Answer to Problem 67AP
The degree of unsaturation in prostaglandin E1 with molecular formula C20H34O5 is 4.
Explanation of Solution
Molecular formula of porostaglandin E1 is C20H34O5. If oxygens are ignored the formula becomes C20H34. A hydrocarbon with twenty carbons will have the molecular formula C20H42. The compound given has four pairs of hydrogens (H42-H34=8) less. So its degree of unsaturation is 4.
The degree of unsaturation in prostaglandin E1 with molecular formula C20H34O5 is 4.
d) Caffeine, C8H10N4O2
Interpretation:
The degree of unsaturation in caffeine, C8H10N4O2, is to be calculated.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of alkanes is CnH2n+2. Knowing this relationship and by working backward the degree of unsaturation in a molecule can be calculated. Each ring or a double bond in a molecule corresponds to a loss of two hydrogens from the formula of alkane. If the compound contains halogens, oxygen and/or nitrogen, then the number of halogens is to be added to the number of hydrogens, the number of oxygens to be ignored and number of the nitrogens is to be subtracted, in arriving at an equivalent hydrocarbon formula.
To calculate:
The degree of unsaturation in caffeine with molecular formula C8H10N4O2.
Answer to Problem 67AP
The degree of unsaturation in caffeine with molecular formula C8H10N4O2 is 6.
Explanation of Solution
Molecular formula of caffeine is C8H10N4O2. If four hydrogens are subtracted for four nitrogens and oxygens are ignored the formula becomes C8H6. A hydrocarbon with eight carbons will have the molecular formula C8H18. The compound given has six pairs of hydrogens (H18-H6=12) less. So its degree of unsaturation is 6.
Conclusion:
The degree of unsaturation in caffeine with molecular formula C8H10N4O2 is 6.
The degree of unsaturation in caffeine with molecular formula C8H10N4O2 is 6.
e) Cortisone, C21H28O5
Interpretation:
The degree of unsaturation in cortisone, C21H28O5 is to be calculated.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of alkanes is CnH2n+2. Knowing this relationship and by working backward the degree of unsaturation in a molecule can be calculated. Each ring or a double bond in a molecule corresponds to a loss of two hydrogens from the formula of alkane. If the compound contains halogens, oxygen and/or nitrogen, then the number of halogens is to be added to the number of hydrogens, the number of oxygens to be ignored and number of the nitrogens is to be subtracted, in arriving at an equivalent hydrocarbon formula.
To calculate:
The degree of unsaturation in cortisone with molecular formula C21H28O5.
Answer to Problem 67AP
The degree of unsaturation in cortisone with molecular formula C21H28O5 is 8.
Explanation of Solution
Molecular formula of cortisone is C21H28O5. If oxygens are ignored then the formula becomes C21H28. A hydrocarbon with twenty one carbons will have the molecular formula C21H44. The compound given has eight pairs of hydrogens (H44-H28=16) less. So its degree of unsaturation is 8.
The degree of unsaturation in cortisone with molecular formula C21H28O5 is 8.
f) Atropine, C17H23NO3
Interpretation:
The degree of unsaturation in atropine, C17H23NO3 is to be calculated.
Concept introduction:
The degree of unsaturation is equal to the number of rings and/or multiple bonds present in the molecule. The general formula of alkanes is CnH2n+2. Knowing this relationship and by working backward the degree of unsaturation in a molecule can be calculated. Each ring or a double bond in a molecule corresponds to a loss of two hydrogens from the formula of alkane. If the compound contains halogens, oxygen and/or nitrogen, then the number of halogens is to be added to the number of hydrogens, the number of oxygens to be ignored and number of the nitrogens is to be subtracted, in arriving at an equivalent hydrocarbon formula.
To calculate:
The degree of unsaturation in atropine with molecular formula C17H23NO3.
Answer to Problem 67AP
The degree of unsaturation in atropine with molecular formula C17H23NO3 is 7.
Explanation of Solution
Molecular formula of atropine is C17H23NO3. If one hydrogen is subtracted for one nitrogen and oxygens are ignored the formula becomes C17H22. A hydrocarbon with seventeen carbons will have the molecular formula C17H36. The compound given has seven pairs of hydrogens (H36-H22=14) less. So its degree of unsaturation is 7.
The degree of unsaturation in atropine with molecular formula C17H23NO3 is 7.
Want to see more full solutions like this?
Chapter 7 Solutions
EBK ORGANIC CHEMISTRY
- Indicate whether each statement is true or false: (a) Fat molecules contain amide bonds. (b) Phosphoplipids can be zwitterions. (c) Phospholipids form bilayers in water in order to have their long hydrophobic tails interact favorably with each other, leaving their polar heads to the aqueous environment.arrow_forwardwhat is the N factor of disodium ethylenediaminetetraacetate (C10H14N2Na2O8)?arrow_forwardDraw structures corresponding to these names:(a) 4-Methylpentanamide (b) N-Ethyl-N-methylpropanamidearrow_forward
- What is the molecular weight of ibuprofen, C13H18O2?arrow_forwardThe structural formula for the open-chain form of D-mannose is CH НО—С—Н Но-с—н Н—С—ОН Н—ҫ—ОН CH-OН (a) Is this molecule a sugar? (b) How many chiral carbons are present in the molecule? (c) Draw the structure of the six-member-ring form of this molecule.arrow_forward(a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl at C17, a double bond between C1 and C2, and methyl groups bonded to C1, C10, and C13. (b) Add wedges and dashed wedges for all stereogenic centers with thefollowing information: the configuration at C10 is R, the configuration at C13 is S, the configuration at C17 is S, and all substituents at ring fusions are trans to each other. (c) Draw the structure of Primobolan, the product formed when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.arrow_forward
- The structural formula for the open-chain form of galactose is CH Н—ҫ—ОН Но—С—н НО—С—Н Н—ҫ—ОН CH-ОН (a) Is this molecule a sugar? (b) How many chiral carbons are present in the molecule? (C) Draw the structure of the six-member-ring form of this molecule.arrow_forward(i) Which one of the following is a disaccharide : Starch, Maltose, Fructose, Glucose?(ii) What is the difference between fibrous protein and globular protein?(iii) Write the name of vitamin whose deficiency causes bones deformities in children.arrow_forwardQ3: Use arrows to match the terms (A) column with (B) column. Some may be used more than once and others not at all. B a- contain glycerol backbone b- glucose é- amino acids d- esters of fatty acids e- octapeptide f- disaccharide 6- Proteins g- polysaccharide k- compound lipids i- steroid-like j- lipids k- polar lipids + glucose storage in animals 7- Cholesterol 8- Lactose 9- Waxes 10AngiotensinlI ((T.O.P)) ((1-2))arrow_forward
- (a) Provide four distinct forms of phenylalanine. (b) Rank the solubility of these forms in water. (c) Explain your ranking.arrow_forward27. Which of the following statements about cholesterol is not correct? CH3 CH3 H. d но Cholesterol (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a -e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.arrow_forwardOne of the cyclic forms of D-ribose has the structure CH2OH OH ОНОН (a) How many anomeric carbon atoms are present in this structure? (b) How many hemiacetal carbon atoms are present in this structure?arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning