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Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.14P
Januvia, the trade name for sitagliptin, was introduced in
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Januvia, the trade name for sitagliptin, was introduced in 2006 for the treatment of type 2 diabetes. (a) Explain why the five-membered ring in sitagliptin is aromatic. (b) Determine the hybridization of each N atom. (c) In what type of orbital does the lone pair on each N atom reside?
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.
Januvia, the trade name for sitagliptin, was introduced in 2006 for the treatment of type 2
diabetes. (a) Explain why the five-membered ring in sitagliptin is aromatic. (b) Determine the
hybridization of each N atom. (c) In what type of orbital does the lone pair on each N atom reside?
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Chapter 17 Solutions
Organic Chemistry-Package(Custom)
Ch. 17 - Prob. 17.1PCh. 17 - What orbitals are used to form the bonds indicated...Ch. 17 - Give the IUPAC name for each compound.Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - How many 13C NMR signals does each compound...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.35PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.63PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- 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 reasonableresonance structures for the ve-membered ring that contains three N atoms.arrow_forward(a)The concept of hybridization was first proposed by Linus Pauling in 1931, that explain about the concept of mixing orbitals to form new hybrid orbital suitable for the pairing of electrons to form chemical bonds. Draw the kekule structure of a compound that contains only carbon and hydrogen atoms that has: (1) One sp hybridize carbon, two sp? hybridized carbons and two sp hybridized carbon (ii) Two sp' hybridized carbon and two sp hybridized carbons (ii) Two sp? hybidized carbons and two sp hybydized carbonarrow_forwardLinoleic acid is an essential fatty acid found in many vegetable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the cis orientation around its two double bonds, where R1 and R2 represent two different groups that form the rest of the molecule. (a) How many different compounds are possible, changing only the cis-trans arrangements around these two double bonds? (b) How many are possible for a similar compound with three double bonds?arrow_forward
- '' Which of the statements A-E is NOT correct about azidothymidine (AZT), an antiviral drug? (a) The molecule contains a sigma bond formed by the overlap of a nitrogen sp orbital with a nitrogen sp2 H3C. NH orbital (b) It contains a secondary (2°) amine (c) It contains a primary (1°) alcohol (d) The molecule contains the following functional groups: alkene, amide, ether (e) It contains one atom with a +1 formal charge and one with a -1 formal charge HOH2C N=N=Narrow_forwardJanuvia is the trade name for sitagliptin, a drug that increases the body's ability to lower blood sugar levels, and thus it was introduced in 2006 for the treatment of type 2 diabetes. (a) Explain why the five-membered ring in sitagliptin is aromatic. (b) Determine the hybridization of each N atom. (c) In what type of orbital does the lone pair on each N atom reside? snimile rios CF3 02.H N. ng art wed HO NH2 0 F to tea roso iw bolcot es eene onwll wbomolhemoa lanothutianoo ori wad sitagliptin CH CH OH H eo OHE 1OM8 w bnod elduob s of bebbs s1s 10 bns 18 lo alnemela erIT g--yrtem-S as doue enexic lsohtemmyanu bns nedw bemot Ishslamarrow_forward(a) How is each N atom in quinine, an effective antimalarial drug that reduces fever, hybridized? (b) In what type of orbital does the lone pair on each N reside?arrow_forward
- The unmistakable odor of a freshly cut cucumber is largely due to cucumber aldehyde. (a) How many sp2 hybridizedcarbon atoms does cucumber aldehyde contain? (b) What is the hybridization of the O atom? (c) What orbitals are used toform the carbon–oxygen double bond? (d) How many s bonds does cucumber aldehyde contain? (e) How many p bondsdoes it contain?arrow_forwardTwo useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCI) and chloroethane (CH;CH;CI). Vinyl chloride is the starting material used to prepare poly (vinyl chloride), a plastic used in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C- Cl bond of vinyl chloride stronger than the C– CIl bond in chloroethane.arrow_forward(a) Draw the nine isomers having the formula C7H16 . (Hint: There is one structure with a seven-carbon chain, two structures with six-carbon chains [one is illustrated in the margin above], five structures with a five-carbon chain, and one structure with a fourcarbon chain.)(b) Identify the isomers of C7H16 that are chiral.arrow_forward
- (a) Label each carbon, oxygen, and nitrogen atom as being sp, sp, or sp hybridized. (b) Circle and identify each functional group by its formal name. (c) Redraw the following compound to be a complete Lewis structure, showing all carbons, hydrogens, bonds, and nonbonded electrons. yo 이니 NECarrow_forwardAromatic compounds must have a p orbital on every atom in the ring. Define this ?arrow_forward(a) Label each carbon, oxygen, and nitrogen atom as being sp, sp, or sp' hybridized. (b) Circle and identify each functional group by its formal name. (c) Redraw the following compound to be a complete Lewis structure, showing all carbons, hydrogens, bonds, and nonbonded electrons. yo NECarrow_forward
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