ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.75P
Interpretation Introduction
Interpretation: The structure of a minor product formed from the radical chlorination of propane which has molecular formula
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
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Identify the structure of a minor product formed from the radical chlorination of propane, which has molecular formula C2H6Cl2 and exhibits the given 1H NMR spectrum.
Although benzene itself absorbs at 128 ppm in its 13C NMR spectrum, the carbons of substituted benzenes absorb either upeld or downeld from this value depending on the substituent. Explain the observed values for the carbon ortho to the given substituent in the monosubstituted benzene derivatives X and Y.
Treatment of alcohol A (molecular formula C5H12O) with CrO3, H2SO4, and H2O affords B with molecular formula C5H10O, which gives an IR absorption at 1718 cm−1. The 1H NMR spectrum of B contains the following signals: 1.10 (doublet, 6 H), 2.14 (singlet, 3 H), and 2.58 (septet, 1 H) ppm. What are the structures of A and B?
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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- Although benzene itself absorbs at 128 ppm in its 13C NMR spectrum, the carbons of substituted benzenes absorb either upfield or downfield from this value depending on the substituent. Explain the observed values for the carbon ortho to the given substituent in the monosubstituted benzene derivatives X and Y.arrow_forwardThe H1H1 NMR spectra corresponds to an alcohol with the molecular formula C5H12O. Deduce the structure from the spectraarrow_forwardDraw the structure of all constitutional isomers that contain a ketone and have molecular formula C5H10O. Give the IUPAC name for each isomer and state how 13C NMR spectroscopy could be used to distinguish these isomers.arrow_forward
- Draw the structure of molecular formula C8H10O that produced the 1H NMR spectra shown below. The IR spectrum does not show a broad absorbance at 3300 cm–1 or a strong absorbance at 1710 cm–1.arrow_forwardNMR of p-iodonitrobenzene Provide the annotated NMR spectra with a drawn structure of your product and clear identification of which protons and carbons in the structure gives rise to which peak in the spectra.arrow_forwardAn unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound that has the following 1H NMR spectrum. What is the structure of the compound?arrow_forward
- Choose the structure corresponding to the given 1H and 13C NMR spectraarrow_forwardExplain why the carbonyl carbon of an aldehyde or ketone absorbs farther downeld than the carbonyl carbon of an ester in a 13C NMR spectrum.arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forward
- A compound reacts with methylmagnesium bromide followed by acidification to form the product with the following 1H NMR spectrum. Identify the compound.arrow_forwardThe 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardYou have a sample of a compound of molecular formula C11H15NO2, which has a benzene ring substituted by two groups, (CH3)2N− and −CO2CH2CH3, and exhibits the given 13C NMR. What disubstituted benzene isomer corresponds to these 13C data?arrow_forward
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