Concept explainers
(a)
Interpretation: The hybridization of carbon atoms of triple bonds 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 pi electrons of the triple bond 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 number of pi electrons that are delocalized in compound A is to be determined.
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
ORG.CHEMISTRY W/ACCESS+MODEL KIT PKG
- 1, 6-Methanonaphthalene has an interesting 1H NMR spectrum in which the eight hydrogens around the perimeter absorb at 6.9 to 7.3 δ, while the two CH2 protons absorb at -0.5 δ. Tell whether it is aromatic, and explain its NMR spectrum.arrow_forwardCompound X (molecular formula C10H12O) was treated with NH2NH2, -OH to yield compound Y (molecular formula C10H14). Based on the 1H NMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardCompound A of molecular formula C3H6O shows a noteworthy infrared absorption at 1716 cm-1. Its 1H-NMR spectrum shows one singlet – δ 2.2 (6H) ppm. Its 13C-NMR spectrum has two signals – δ 30, 207 ppm. Suggest a structure for this compound.arrow_forward
- Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardCompound P has molecular formula C5H9C102. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardCompound B has molecular formula C9H10. The IR spectrum is shown below. The 1H-NMR spectrum shows a multiplet at 7.2 ppm integrating to 4H, a triplet at 2.9 ppm integrating to 4H, and a triplet at 2.1 ppm integrating to 2 H. Suggest a structure for B and explain your reasoningarrow_forward
- The shrub ma huang (Section 5.4A) contains two biologically activestereoisomers—ephedrine and pseudoephedrine—with two stereogeniccenters as shown in the given structure. Ephedrine is one component ofa once-popular combination drug used by body builders to increaseenergy and alertness, whereas pseudoephedrine is a nasaldecongestant.a.) Draw the structure of naturally occurring (−)-ephedrine, which has the1R,2S configuration.b.) Draw the structure of naturally occurring (+)-pseudoephedrine, whichhas the 1S,2S configuration.c.) How are ephedrine and pseudoephedrine related?d.) Draw all other stereoisomers of (−)-ephedrine and (+) pseudoephedrine, and give the R,S designation for all stereogeniccenters.e.) How is each compound drawn in part (d) related to (−)-ephedrine?arrow_forwardAn unknown compound A (molecular formula C7H14O) was treated with NaBH4 in CH3OH to form compound B (molecular formula C7H16O). Compound A has a strong absorption in its IR spectrum at 1716 cm−1. Compound B has a strong absorption in its IR spectrum at 3600−3200 cm−1. The 1H NMR spectra of A and B are given. What are the structures of A and B?arrow_forwardThe compound MON-0585 is a non-toxic, biodegradable larvicide that is highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromatic rings.arrow_forward