Compound A (C9H12) shows prominent peaks in its mass spectrum at m/z 120 and 105. Compound B (also C9H12) shows prominent peaks at m/z 120 and 91. On vigorous oxidation with chromic acid, both compounds give benzoic acid. From this information, deduce the structural formulas of compounds A and B.

Compound A (C9H12) shows prominent peaks in its mass spectrum at m/z 120 and 105. Compound B (also C9H12) shows prominent peaks at m/z 120 and 91. On vigorous oxidation with chromic acid, both compounds give benzoic acid. From this information, deduce the structural formulas of compounds A and B.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

See similar textbooks

Related questions

Q: For each cnemical reaction listed in the table below, decide whether the highlighted atom is being o...

A: The substance whose oxidation increases in the reaction loses electrons. And since loss of electron ...

Q: Testosterone, the male sex hormone, contains only C, H, and O. It is 79.12% C and 9.79% H by mass. E...

A: Testosterone, the male sex hormone, contains only C, H, and O. The % mass composition is given as f...

Q: The U. S. Environmental Protection Agency (EPA) sets limits on healthful levels of air pollutants. T...

A: Given: Total volume is 5.60 L. Mass of lead per m3 is 1.5 µg/m3.

Q: calculate the wavelength of a photon that has three times as much energy as that of a photon of a wa...

A: The energy of photon is given by

Q: At 500k the reaction has kp=0.497.in an equilibrium mixture at 500k ;the partial pressure of PCL5 ...

Q: A certain alloy with a density of 11.5 g/cm3 contains 55% iron by mass. a) How many pg of iron would...

A: Density is defined as the mass per unit volume. It is represented by rho . Its relation is as follow...

Q: The ratio of isotopic abundance of elements can vary throughout the solar system (Table 1). The prot...

A: Atomic mass of any substance is given by the abundance average mass of its available isotopes.

Q: 24 The electron configuration of element Y ends in sp. What is the symbol for the ion most commonly ...

Q: McQuane ROCK dlogly Balance the equation for a half-reaction that occurs in acidic solution. Use e a...

Q: 15) H2O (H2 O) is a weaker acid than HF ("H" "F"). Question 15 options: True False

A: According to the Arrhenius and Brønsted-Lowry Concepts of acids, the species which release H+ ions a...

Q: When the compound shown below undergoes acid-catalyzed dehydration, a ring expansionoccurs to give t...

A: This is acid catalyzed ring expansion reaction. Mechanism :

Q: How do I do this problem? Determine the empirical formula of a compound having the following percent...

A: Empirical formula: Formula of a compound in which the ratio of number of constituent elements is sho...

Q: Please convert the following compound from its condensed structural formula into its expanded formul...

A: Interpretation: The given condensed structural formula is to be converted to its expanded formula. G...

Q: Identify one of the two common products of a combustion reaction of a hydrocarbon.

Q: Predict the chemical formula for the ionic compound formed by Cu²⁺ and P³⁻

Q: The contents of one 90. lb bag of topsoil will cover 10. square feet of ground to a depth of 1.7 in....

A: Given : 1 bag of topsoil will cover area = 10 ft2 And the depth covered by 1 topsoil cover = 1.7 in...

Q: Write the ionic equation that would result from the following: Hg(NO3)2 (aq) + 2 NaI (aq) --> 2...

A: Ionic compound dissociates into their constituent ions when dissolved in the aqueous medium. Solid p...

Q: Calculate the percent composition of all elements in lead(II) chromate.

A: % of an element in compound = (100 x Total mass of Element)/Molar mass of compound Formula of Lead (...

Q: What is the systematic IUPAC name for:

A: 1) In the first compound we can see that the longest possible carbon chain i.e parent chain is of 11...

Q: In this question: "How many O atoms are in 24.34 g of sucrose, C12H22O11?" Why is the answer not 11,...

Q: Alkanes are essentially inert compounds (they do not react). Why is this?

A: Alkanes are hydrocarbon formed by the carbon and hydrogen atoms. In alkane, the carbon atoms of the ...

Q: I have no idea how to enter these into my calculater to get the correct answer. The rearrangement of...

A: Given: The reaction is first order. Initial concentration = 0.179 M Final concentration = 0.0292 M T...

Q: When HCl is added to an alkene in a Markovnikov reaction, the product will have a higher boiling poi...

A: There are two main factors that govern boiling point: 1. Molecular weight of compound (In general bp...

Q: Industrially, nitric acid is produced by the Ostwald process, as represented by the following equati...

A: The theoretical yield of a reaction can be calculated as follows. Theoretical yield=actual yieldperc...

Q: A compound is found to contain 7.523 % phosphorus and 92.48 % iodine by weight.What is the empirical...

Q: assuming the volume is 1 dm3, calculate the equilibrium constant for the reaction of A2+ 2A (g) >...

Q: Write the net ionic equation representing the neutralization of any strong acid with an ionic hydrox...

A: This is acid-base reaction. We can take the basic example of hydrochloric acid reaction with sodium ...

Q: Can i get help with these problems

A: Ions are charged species which can be both positively or negatively charged. These are of two types....

Q: Which solution could be used to precipitate the barium ion, Ba2+, in a water sample: sodium chloride...

Q: Draw bond line structure for : 3,4-diethyl-3,5-dimethylheptane

A: The bond line structure represents the structure of the organic compound in line notation. Every ver...

Q: What is [H3O+] in a solution of 0.075 M HNO2 and 0.030 M NaNO2? Kb=4.5 * 10-5

A: Given, 0.075 M HNO2 0.030 M NaNO2

Q: What is the molality of lithium ions in a 0.302 m solution of Li₃PO₄ assuming the compound dissociat...

A: Ionization of Li3PO4 can be shown as: Li3PO4 = 3Li+ + PO43- Thus, one mole of Li3PO4 after i...

Q: 10) Find the p H of a 0.291 M N a A solution. The salt completely dissociates into N aplusand Aminus...

Q: Calculate the number of atoms in a 2.17 x 105 mole sample of neon. Your answer should be rounded to ...

A: Number of moles of a substance is equal to the mass of the substance divided by its molar mass.

Q: Calculate the percentage composition for C2H6O .

Q: 1.Which of the following liquids are likely to be miscible with water: 1-propanol(CH3CH2CH2OH), carb...

A: Hey, since there are multiple questions posted, we will answer first question. If you want any speci...

Q: A mixture of carbon dioxide and xenon gases, at a total pressure of 1,407 mmHg, contains 2.18 g of c...

Q: Propose a plausible step by step mechanism for the following transformation. H30+, heat

Q: The following reactions poccur in aqueous solution. Complete and balance the molecular equations usi...

Q: 9) The weak acid, H A, has a K a value of 1.6E-5. Calculate the pH of the solution if the concentrat...

Q: explain why sulfonate esters are such good leaving groups, in terms of structure and bonding

A: Sulfonic esters are derivatives of sulfonic acids. Sulfonate esters contain a sulfur with two double...

Q: For the reaction shown, calculate how many moles of NH3 form when each amount of reactant completely...

Q: Calculate the number of moles of Cl atoms in 2.41×1024 formula units of magnesium chloride, MgCl2

A: Avogadro's number gives the number of atoms, molecules or ions in one mole of the substance and it ...

Q: 12) Do you expect KBr ( OR K Br) to be acidic, neutral, or basic when dissolved in pure water? ...

A: KBr is an ionic salt formed by the neutralization reaction between strong acid hydrogen bromide HBr ...

Q: Chlorine gas reacts with fluorine gas to form chlorine trifluoride. Cl2 (g) + 3 F2 (g) → 2 ClF3 (g)...

Q: Convert and watch for sig figs! Answer in scientific notation. 134.7 kJ is kcal

A: Given units are KJ and Kcal and they are units of energy. For converting KJ to Kcal (thermochemical...

Q: a rain drop has a mass of 50mg and the entire pacific ocean has a mass of 7.08e20kg. What is the mas...

A: The mass of the rain drop is 50 mg = 0.05 g. The mass of entire Pacific Ocean is 7.08 × 1020 Kg.

Question

Compound A (C₉H₁₂) shows prominent peaks in its mass spectrum at m/z 120 and 105. Compound B (also C₉H₁₂) shows prominent peaks at m/z 120 and 91. On vigorous oxidation with chromic acid, both compounds give benzoic acid. From this information, deduce the structural formulas of compounds A and B.

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Trending now

This is a popular solution!

Step by step

Solved in 4 steps with 3 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Following are IR and 1H-NMR spectra of compound D. The mass spectrum of compound D shows a molecular ion peak at m/z 136, a base peak at m/z 107, and other prominent peaks at m/z 118 and 59. Q.) Propose structural formulas for ions in the mass spectrum at m/z 118, 107, and 59.
Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.
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.
Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?
Draw the structure of a compound with the formula C5H10O2 (along with the reasons of choosing it) which, upon analysis, gave key peaks in an infrared spectrum at 3450 cm-1 and 1713 cm-1, as well as the following 1H-NMR spectrum.
Propose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3
Propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Please assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.
Please propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.
Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below. Suggest a structure for C and explain your reasoning.
Deduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.
Predict the characteristic infrared absorptions of the functional groups in the following molecules. (a) pent-1-yne (b) diethylamine
Following 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.