(a)
Interpretation:
The differences in the structural formula of testosterone and methandrostenolone should be determined along with
Concept Introduction:
Steroids are the third major class of lipids. These are the compounds containing the following ring system:
Answer to Problem 70P
Both methandrostenolone and testosterone hormone contains hydroxyl functional group (alcohol) and carbonyl functional group (kentone).
In the structural formula of testosterone hormone, there is only one double bond and it has only one methyl group attached to cyclopentane ring whereas in methandrostenolone there are two double bonds and two methyl groups are attached to the cyclopentane ring.
Explanation of Solution
Testosterone and methandrostenolone both the hormones contain one −OH group attached to cyclopentane ring and one >C=O group in cyclohexene ring. Therefore both alcoholic and
In the structure of testosterone there is only a double bond in cyclohexene ring having ketonic group and no methyl group is present on the carbon of cyclopentane ring having alcoholic group as shown:
In the structure of methandrostenolone, there are two double bonds in cyclohexene ring having ketonic group and one methyl group attached on the carbon of cyclopentane ring having alcoholic group as shown:
(b)
Interpretation:
In both the given hormones mark all the stereocenters and state the number of stereoisomer possible for each.
Concept Introduction:
Stereoisomers are the compounds that are differ only in the spatial arrangement of their atoms. Each stereoisomer has at least one stereocenter. A stereocenter is a tetrahedral carbon atom that has four different groups bonded to it. For a molecule with n sterocenters, a maximum of
Answer to Problem 70P
Stereocenters in testosterone:
Since testosterone has six stereocenters therefore it has 64 possible stereoisomers.
Stereocenters in methandrostenolone:
Since methandrostenolone has six stereocenters therefore it has 64 possible stereoisomers.
Explanation of Solution
A stereocenter is a tetrahedral carbon atom that has four different groups bonded to it.
Stereocenters in testosterone:
In testosterone there are six stereocenters.
For a molecule with n stereocenter, a maximum of
Stereocenters in methandrostenolone:
In methandrostenolone there are six stereocenters.
For a molecule with n stereocenter, a maximum of
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Chapter 16 Solutions
Introduction To General, Organic, And Biochemistry
- For each of the following, indicate whether the arrow pushes are valid. Do we break any rules via the arrows? If not, indicate what is incorrect. Hint: Draw the product of the arrow and see if you still have a valid structure. a. b. N OH C. H N + H d. e. f. مه N COHarrow_forwardDecide which is the most acidic proton (H) in the following compounds. Which one can be removed most easily? a) Ha Нь b) Ha Нь c) CI CI Cl Ha Ньarrow_forwardProvide all of the possible resonanse structures for the following compounds. Indicate which is the major contributor when applicable. Show your arrow pushing. a) H+ O: b) c) : N :O : : 0 d) e) Оarrow_forward
- Draw e arrows between the following resonance structures: a) b) : 0: :0: c) :0: N t : 0: بار Narrow_forwardDraw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. Cl Substitution will not occur at a significant rate. Explanation Check :☐ O-CH + Х Click and drag to start drawing a structure.arrow_forwardDraw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. Cl C O Substitution will not occur at a significant rate. Explanation Check + O-CH3 Х Click and drag to start drawing a structure.arrow_forward
- ✓ aw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. C Cl HO–CH O Substitution will not occur at a significant rate. Explanation Check -3 ☐ : + D Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Cearrow_forwardPlease correct answer and don't used hand raitingarrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- Determine whether the following reaction is an example of a nucleophilic substitution reaction: Br OH HO 2 -- Molecule A Molecule B + Br 义 ollo 18 Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. Which of the reactants is referred to as the nucleophile in this reaction? Which of the reactants is referred to as the organic substrate in this reaction? Use a ŏ + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. ◇ Yes O No O Molecule A Molecule B Molecule A Molecule B टेarrow_forwardPlease correct answer and don't used hand raitingarrow_forwardPlease correct answer and don't used hand raitingarrow_forward
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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