Interpretation:
Chiral carbon atoms present in nepetalactone has to be labelled. The number of possible stereoisomers for nepetalactone has to be given and to show that nepetalactone is a terpene.
Concept Introduction:
Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.
Isoprene unit:
Branched end of isoprene – Head
Unbranched end of isoprene - Tail
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,
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Chapter 5 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- The molecule 2,5-dibromohex-3-ene contains three stereogenic sites: a double bond that can be cis- or trans- and two chirality centers that can be either (R) or (S). Draw structures for and name all possible stereoisomers of 2,5-dibromohex-3-ene. HINT: That means a possible total of 2³ stereoisomers, but there's also the potential for high symmetry or meso stereoisomers, which then reduces the total number of possibilities. Put boxes around pairs of enantiomers, and label meso compounds as "meso," as appropriate.arrow_forwardGive the stereochemical relationships between each pair of structures. Examples are same compound, structural isomers, enantiomers, diastereomers. Which pairs could you (theoretically) separate by distillation or recrystallization?*refer to the photo belowarrow_forwardWrite the name of the following compounds. Which of them are stereoisomers? Which of them are optically active? Use cis-trans, (E)(Z) nomenclature and assign the absolute configuration (R),(S), if any to each chiral center.arrow_forward
- assign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither.arrow_forwardassign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither.arrow_forwardPyrethrins, such as jasmolin II(below), are a group of naturalcompounds synthesized by flowers of the genus Chrysanthemum(known as pyrethrum flowers) to act as insecticides.(a) Circle and name the functional groups in jasmolin II.(b) What is the hybridization of the numbered carbons?(c) Which, if any, of the numbered carbons are chiral centers?arrow_forward
- (a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?arrow_forward2. Explain with a couple of acyclic or cyclic examples (5 carbons or more) what is crit- ical for you when establishing whether a molecule is chiral or acral.arrow_forwardIs pentanoic acid a chiral molecule or not?arrow_forward
- Pyrethrin II and pyrethrosin are two natural products isolated from plants of the chrysanthemum family. Pyrethrin II is a natural insecticide and is marketed as such. Q,) Label all chiral centers in each molecule and all carbon-carbon double bonds about which there is the possibility for cis,trans isomerism.arrow_forwardDraw a structural formula for 3-chloro-3-methylhexane.arrow_forwardDraw three-dimensional representations of the following compounds. Which have asymmetric carbon atoms? Which have no asymmetric carbons but are chiral anyway? Use your models for parts (a) through (d) and any others that seem unclear.1,3-dichloropropadienearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
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