Concept explainers
(a)
Interpretation: The hybridization of each nitrogen atom in methotrexate is to be predicted.
Concept introduction: Hybridization is the combination of two or more atomic orbitals to form the same number of hybrid orbitals, each having the same shape and energy. Number of groups around the atom is equal to number of the number of orbitals hybridized to give hybrid atomic orbitals.
(b)
Interpretation: The type of orbital in which the lone pair of nitrogen atom resides is to be predicted.
Concept introduction: Hybridization is the combination of two or more atomic orbitals to form the same number of hybrid orbitals, each having the same shape and energy. Number of groups around the atom is equal to number of the number of orbitals hybridized to give hybrid atomic orbitals.
(c)
Interpretation: The reason corresponding to the fact that the bicyclic ring in methotrexate is
Concept introduction: A molecule must be cyclic, planar, completely conjugated and should follow
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
ORGANIC CHEMISTRY
- Rizatriptan (trade name Maxalt) is a prescription drug used for the treatment of migraines. (a) How many aromatic rings does rizatriptan contain? (b) Determine the hybridization of each N atom. (c) In what type of orbital does the lone pair on each N reside? (d) Draw all the resonance structures for rizatriptan that contain only neutral atoms. (e) Draw all reasonable resonance structures for the five-membered ring that contains three N atoms.arrow_forward2) State if the following compounds are aromatic, non-aromatic, or anti-aromatic. (a) S: (b) ΗΝarrow_forward5) Which of the following compounds is aromatic? B C H Darrow_forward
- Ciprofloxacin is a member of the fluoroquinolone class of antibiotics.(a) Which of its rings are aromatic?arrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forwardWhich of the following are aromatic?arrow_forward
- Determine the weakest C-H bond in each of the following compounds. (a) (b) (c) ОНarrow_forwardUnder certain reaction conditions, 2,3-dibromobutane reacts with two equivalents of base to give three products, each of which contains two new p bonds. Product A has two sp hybridized carbon atoms, product B has one sp hybridized carbon atom, and product C has none. What are the structures of A, B, and C?arrow_forwarda) Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Give reasons for each answer.arrow_forward
- The enamine prepared from acetone and dimethylamine is shown here in its lowest-energy form. (a) What is the geometry and hybridization of the nitrogen atom? (b) What orbital on nitrogen holds the lone pair of electrons? (c) What is the geometric relationship between the p orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?arrow_forwardAcridine is a heterocyclic aromatic compound obtained from coal tar that is used in the synthesis of dyes. The molecular formula of acridine is C13H9N, and its ring system is analogous to that of anthracene except that one CH group has been replaced by N. The two most stable resonance structures of acridine are equivalent to each other, and both contain a pyridine-like structural unit. Write a structural formula for acridine.arrow_forwardCyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three ℼ-electronarrow_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