Interpretation:
A structure for the compound A, C4H8O3, with the following spectral characteristics is to be proposed.
I R: 1710 cm-1, 2500 cm-1, 3100 cm-1.
1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).
Concept introduction:
In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm-1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm-1.
In 1HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ.
To propose:
A structure for the compound A, C4H8O3, with the following spectral characteristics is to be proposed.
I R: 1710 cm-1, 2500 cm-1, 3100 cm-1.
1HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).
Trending nowThis is a popular solution!
Chapter 20 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene. Show all reagents and all intermediate structures. Assume that ortho and para isomers can be separatedarrow_forwardThe unknown compound with molecular formula C4H8O3, has infrared absorptions at 1710 and 2500 to 3100 cm^-1 and has ¹H NMR spectrum shown. Analyze the given data and propose a structure for this compound. Explain how you come up with your proposed compound.arrow_forwardCompound A has molecular formula C5H8Br4 but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.arrow_forward
- Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardIdentify the structures of D and E, isomers of molecular formulaC6H12O2, from their IR and 1H NMR data. Signals at 1.35 and 1.60 ppm inthe 1H NMR spectrum of D and 1.90 ppm in the 1H NMR spectrum of Eare multiplets.arrow_forwardCompound p,c6h14O does not react w/sodium metal,doesn't discharge the color of Br2 in ccl4, the H-NMR spectrum shows 2 signal,a 12H doublet at 1.1, and a 2h sextet at 3.6. Propose a structure for this compound,p.arrow_forward
- Compound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and Darrow_forwardIdentify the pericyclic reaction benzocyclobutane E undergoes on heating, give astructure for intermediate H, and provide a mechanism that accounts for itsformation.arrow_forwardFollowing are 1H-NMR spectra for compounds B (C6H12O2) and C (C6H10O). Upon warming in dilute acid, compound B is converted to compound C. Deduce the structural formulas for compounds B and C.arrow_forward
- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardAn optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.arrow_forwardCompound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughoutarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning