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.
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Chapter 7 Solutions
Organic Chemistry
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