Concept explainers
(a)
Interpretation:
The
Concept Introduction:
Amide: One
Depending on the number of carbon side chain of the nitrogen, different types of amines can form.
Hemiacetal is an organic compound with a general formula
Alcohol: It is an organic compound where it contains at least one
(b)
Interpretation:
Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.
Concept Introduction:
Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.
Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.
Number of possible stereoisomers for a compound can be determined as,
Enantiomers: They are chiral molecules whose mirror images are not superimposable.
Number of possible enantiomers for a compound can be determined as,
(c)
Interpretation:
The alternative chair conformations for desosamine have to be drawn.
Concept Introduction:
Drawing Axial and Equatorial substituents:
Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.
(c)
Interpretation:
More stable alternative chair conformations for desosamine have to be identified and explained.
Concept Introduction:
Drawing Axial and Equatorial substituents:
Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.
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Chapter 23 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
- (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(a) Consider structure Y. OH CH3 C-0-CH3 Structure Y i. Redraw structure Y, circle and name all the functional groups that exist in Y. ii. Label the chiral carbons in asterisks(*).arrow_forwardWhich statements are true about constitutional isomers? (a) They have the same molecular formula. (b) They have the same molecular weight. (c) They have the same order of attachment of atoms. (d) They have the same physical propertiesarrow_forward
- 4. (a) Draw all possible isomers of C4H3CI2. (b) Indicate which pairs of compounds are enantiomers of one another. (c) Indicate which pairs of compounds are diastereomers of one another. (d) Indicate which compounds would have optical rotations of 0°. (e) Assign R and S configurations to all chirality centers of the compounds in part (a).arrow_forwardClassify each attached pair of compounds as stereoisomers or conformations: (a) X and Y; (b) X and Z.arrow_forward1. Some marine plankton contain triacylglycerols formed from the polyunsaturated fatty acid (PUFA) such as: CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2COOH a) Draw the skeletal structure of the given PUFA showing the preffered stereogenic arrangement for a naturally-occuring lipid at each double bond. b) Write the systematic name of the fatty acid. c) What type of omega-n acid is this fatty acid? d) Would you expect this fatty acid to be a soild or liquid at room temperature?arrow_forward
- a) Give the chemical structure for each of the following compound: (i) 4-hydroxybenzoic acid (ii) 2-hexene (iii) chlorocyclohexane (iv) 2,5-dichloroheptane b) Prostaglandin are a group of C20 lipids and can be found in small amounts in all body tissues and fluids. (1) Put an asterisk on all the chiral carbon(s) present in the chemical structure of prostaglandin E. (II) Do you expect prostaglandin to be acidic or basic? (III) Circle the functional group that is responsible for the acidity / basicity. ali se odno HO OH HO Prostaglandin Earrow_forwardFor each of the following compounds,determine whether each is optically active. For optically active compounds, identify the chiral carbon: ethane, 2-chloro-2-methylbutane, CH3CH(NH2)COOH, CH3CH2CHClCH3and CH3CH2CH2CH3. And for non-optical active compounds, just provide the structure of the compoundarrow_forward(a) Locate the isoprene units in lycopene, the red pigment in tomatoes. (b) Which isoprene units are connected in a head-to-tail fashion? (c) Label any other isoprene unit as connected in a head-tohead fashion or a tail-to-tail fashion. (d) Classify lycopene as a monoterpene, sesquiterpene, and so on.arrow_forward
- Which objects are asymmetric (have no plane of symmetry): (a) a circular clock face; (b) a football; (c) a dime; (d) a brick; (e) a hammer; (f) a spring?arrow_forwardHow many chiral centers are present in this molecule? (a) (b) two (c) (d) one three none Angearrow_forwardThiols are sulfur containing organic compounds. Allyl mercaptan is a small molecule from garlic and responsible for “garlic breath”. Its formula is C3H6S. It has been shown to be the most effective HDAC (Histone deacetylase inhibitors) inhibitor of known garlic-derived organosulfur compounds and their metabolites. Draw all possible isomers with formula C3H6S. Define among the molecules which could be optically active. Which of molecule is allyl mercaptan?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning