Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 21, Problem 21.78P
An unknown compound D exhibits a strong absorption in its
of D shows a molecular ion at
below. What is the structure of D?
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An unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z =150 and a base peak at 121. The 1H NMR spectrum of D is shown below.What is the structure of D?
An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H NMR spectrum of D is shown below. What is the structure of D?
Compound X (molecular formula C10H120) was treated with NH2NH2, ¯OH to yield compound Y (molecular formula C10H14). Match
the 1H NMR spectra of X and Y to the corresponding structures of X and Y.
Compound NH2NH2 Compound
'H NMR of X
6 H
OH
Y
1 H
5H
8.
6.
4
ppm
or
H NMR of Y
6 H
2H
5H
1 H
multiplet
multiplet
8.
6.
4.
3.
1
nnm
2.
2.
3,
O:
Chapter 21 Solutions
Organic Chemistry
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Problem 21.17 Draw the products of the following...Ch. 21 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 21 - Problem 21.19 Draw the products (including...Ch. 21 - Problem 21.20 What starting materials are needed...Ch. 21 - Prob. 21.21PCh. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Prob. 21.34PCh. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.36PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.39PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.42PCh. 21 - 21.43 Give the IUPAC name for each compound.
a....Ch. 21 - 21.44 Give the structure corresponding to each...Ch. 21 - Prob. 21.45PCh. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.47PCh. 21 - 21.48 Draw all stereoisomers formed in each...Ch. 21 - Prob. 21.49PCh. 21 - What products are formed when each acetal is...Ch. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.54PCh. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.60PCh. 21 - Devise a synthesis of each compound from ethanol...Ch. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.66PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.69PCh. 21 - Prob. 21.70PCh. 21 - Prob. 21.71PCh. 21 - Prob. 21.72PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.79PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.82PCh. 21 - 21.83 Draw a stepwise mechanism f or the...Ch. 21 - Prob. 21.84PCh. 21 - Prob. 21.85PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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- 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_forwardKetones 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?arrow_forwardAnethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.arrow_forward
- Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forward22. A compound with the molecular formula C8H8O produces an IR spectrum with signals at 3063, 1686, and 1646 cm-1. The 1H NMR spectrum of this compound exhibits a singlet at 2.6ppm(l=3H), and a multiplet at 7.5(l= 5H). Draw the structure and give the common name of this compound . Show the correlations between the structure and spectra.arrow_forwardAn unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this data?arrow_forward
- The '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_forwardAn unkown compound, which is insoluable in water but soluble in 10% aqueous sodium bicarbonate, yielded the given 1H NMR spectrum. What is the compound?arrow_forwardTreatment of butan-2-one (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectrum of Q are given below. What is the structure of Q?arrow_forward
- Treatment of butan-2-one (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectra of Q are given below. What is the structure of Q?arrow_forwardWhat is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150–2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?arrow_forwardTreatment of butan-2-one (CH3COCH2CH3) with strong base followed byCH3I forms a compound Q, which gives a molecular ion in its massspectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectra of Q aregiven below. What is the structure of Q?arrow_forward
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