Concept explainers
(a)
Interpretation : The structure of ( R )-2-chloropentane needs to be drawn.
Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their
(b)
Interpretation : The structure of ( S )-2-methyl-3-bromohexane needs to be drawn.
Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.
(c)
Interpretation : The structure of (S)-1,3-dichlorobutane should be drawn.
Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.
(d)
Interpretation:The structure of(R)-2-chloro-1,1,1-trifluoro-3-methylbutane should be drawn.
Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.
Want to see the full answer?
Check out a sample textbook solutionChapter 5 Solutions
Organic Chemistry: Structure and Function
- 12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?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_forward(a) (R)-1,1,2-trimethylcyclohexane, draw a three-dimensional representation.arrow_forward
- For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutanearrow_forwarda) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward
- Which of the following compounds has a stereoisomer that is a meso compound? (I) 1,2- dibromocyclohexane, (II) 1,4-dibromocyclohexane, (III) 2,3-dibromobutane, (IV) 2,3-dimethylbutane, (V) 3,4-dimethylhexane. Recall that an achiral species is one that just contains an internal plane of symmetry. However, a meso compound has two or more asymmetric centers and an internal plane of symmetry. I only O l and II I and III I, III, and V O IV onlyarrow_forward2A2: Apply the concepts of stereocenters, chirality, asymmetry, and the CIP Rules to label enantiomers/ diastereomers and R/S or E/Z absolute configurations. These two (2) structures have ambiguous configurations. Provide a wedge and dash structure for the indicated configurational isomer. In your response, keep the overall structural orientation the same as given. In addition, label all alkenyl FGs as either E or Z in both structures by showing your work. & H3 C CH3 (R, R, R,) H3CO. H3CO CH3 (S, S, S) CH3 OCH 3 OCH 3arrow_forward(a) How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.arrow_forward
- Draw two cyclic constitutional isomers of trans-1,2-dimethylcyclopentane with the same size ring. • In cases where there is only one cyclic constitutional isomer, just draw one structure. • If there are more than two isomers, draw any two of the possible structures. • Your drawing must specify cis/trans stereochemistry unambiguously using wedged and dashed bonds. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. ? ChemDoodle it'sarrow_forwardDraw the structure of the following compounds all showing C and H atoms.(a) 2-methyl -3-iso propyl heptanes(b) Dicyclopropyl methane.arrow_forward(c) Answer the following questions: It is possible for a compound to be chiral even though it lacks a carbon atom with four different groups. Using two nitro groups, one isopropyl group and one carboxy group as substituents, draw the structure of an optically active biphenyl that is void of a chiral carbon. i. ii. Deduce, giving reasons, whether or not the following molecules are optically active. H3C CH3 ČH(CH3)2 Quaternary ammonium salt NH2 Compound A НОСІНС OCH3 OCH3 Br Compound Barrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY