Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 23, Problem 3LGP
Interpretation Introduction
Interpretation:
On the basis of given information, the structures of the required terpene and its isoprene unit are to be elucidated.
Concept introduction:
Terpenes are largely found as constituents of essential oils. They are mostly hydrocarbons.
The building block is a five-carbon isoprene unit
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The oxidation of 3-pentanol to 3-pentanone was performed in the lab and an IR was taken of the finished product.
(a) what are the key functional groups in the starting material, 3-pentaol?
(b) what are the key functional groups in the product, 3-pentanone?
(c) based on the IR spectrum below, was the experiment successful, and, if so, how pure was the product? Explain your reasoning.
and
An acidic liquid has a broad band at 3300 cm
a sharp band at 1710 cm in the infrared spectrum.
One mole of this unknown reacts with one mole of
NaOH. The ¹H NMR spectrum shows three peaks
in the ratio 2 : 2 : 1. Microanalysis gave C, 33.2 %;
H, 4.6%; C1, 32.7%.
Deduce the structure of the unknown.
Spell out the full name of the compound.
(d)
Ozonolysis of 3,4-dimethyl-3-hexene gives compound D.
(i)
Write the reaction step for the formation of D by including the
appropriate reagents.
(ii)
The mass spectrum of compound D shows a fragment ion peak at m/z
57. Propose the structure of this fragment ion.
(ii)
Identify the more stable resonance of the proposed structure in (ii).
Chapter 23 Solutions
Organic Chemistry
Ch. 23 - Prob. 1PPCh. 23 - Prob. 2PPCh. 23 - Prob. 3PPCh. 23 - Prob. 4PPCh. 23 - Prob. 5PPCh. 23 - Prob. 6PPCh. 23 - Prob. 7PPCh. 23 - Prob. 8PPCh. 23 - Prob. 9PPCh. 23 - Prob. 10PP
Ch. 23 - Prob. 11PPCh. 23 - Prob. 12PPCh. 23 - Prob. 13PPCh. 23 - Prob. 14PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - When limonene (Section 23.3) is heated strongly,...Ch. 23 - Gadoleic acid (C20H38O2), a fatty acid that can be...Ch. 23 - 23.20 -Phellandrene and -phellandrene are isomeric...Ch. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Prob. 27PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGP
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
- Name the following compounds A and B. How could you distinguish these two molecules by using 1H NMR and IR techniques? Propose an analytical technique to determine the iron content of these compounds. Calculate the mass percentages of C and H of compound B (C: 12.01 g/mol; H: 1.008 g/mol; Fe: 55.845 g/mol).arrow_forwardA compound of mass 149 has the following elemental analysis : C = 80.48%, H=10.13%, N=9,39%. The IR, 1H and 13C NMR spectra are given below. In the 13C spectrum decoupled from the 1H the nature of the carbon was determined using the 13C DEPT spectra (not shown here). Assign the spectra and identify the compound. You can: 1) Calculate the molecular formula of compound A; 2) Calculate the unsaturation number; 3) Analysethe characteristic bands of the IR spectrum; 4) Assign and interpret all the data from the 1H and 13C NMR spectra). 3500 1800 1600 1400 1200 1000 800 600 cm¹ го протру AU I=3 I=1 I=1 4.0 8.0 I=2 I=2 71 150 3000 с 7.0 CH C 125 2500 6.0 CH 2000 2,8; 40 ppm 5.0 100 Explain why the answer Is this one : 4,5 (6,8; 115) C CH3-NH THÀ ppm ppm 75 3.0 7,2; 128) 132 50 CH₂ 2.0 CH CH₂ 25 CH 3 -CH 3,2; 27 CH3 I=6 1.0 1,2; 22arrow_forwardDo (8) (b) asap pleasearrow_forward
- 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.arrow_forwardShown below is th carbon NMR spectrum of a compound of the formula C7H14. The compound decolorizes a solution of bromine in dichloromethane. Assign a structure to this hydrocarbon. Correlation of spectrum with number of hydrogen atoms attached to each carbon=arrow_forwardSuggest structures given the 1H NMR spectra and formulas for each of the compounds below. C9H10Oarrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forward10. For each of the following mixtures, suggest a separation technique and explain a basis for your choice: (a) Acetone (a volatile liquid) and benzaldehyde (b) N-Ethylpentanamine, butanamide and phenol. Explain.arrow_forwardAnnotate the NMR spectra. Assign the hydrogens to the structure of methyl 3-nitrobenzoate.arrow_forward
- (b) Ozonolysis of 2,7-dimethyl-4-octyne gave compound E. 0 Show the reaction involved for the formation of compound E. (i) By using the IR spectra of the reactant and product, determine the differences in their absorption bands when the reaction is completed.arrow_forwardThe following is the mass spectrum of compound C, C,H,O. Compound C is infinitely soluble in water, undergoes reaction with sodium metal with the evolution of a gas, and undergoes reaction with thionyl chloride to give a water-insoluble chloroalkarne. Propose a structural formula for compound C and write equations for each of its reactions. 100 31 80 60 40 20 M (60) 10 20 30 40 m/z 50 60 70 80 Relative Abundancearrow_forwardA hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning