Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 14, Problem 14.27P
How many lines are observed in the
a. b. c. d.
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Answer the following questions for each compound: a. How many signals are in its 13C NMR spectrum? b. Which signal is at the lowest frequency?
How many signals are expected in the ¹H NMR spectrum of each of the
following compounds?
a.
b.
d.
OA: 2 signal, B: 8 signal, C: 4 signal, D: 2 signal
A: 1 signal, B: 5 signal, C: 4 signal, D: 2 signal
OA: 2 signal, B: 8 signal, C: 4 signal, D: 4 signal
OA: 2 signal, B: 8 signal, C: 6 signal, D: 2 signal
B.21 How would each of the following pairs of compounds differ in their IR
spectra?
a.
b.
C.
d.
and
OH
OCH 3
and
-OCH3 and
and
OCH3
OCH₂
EN
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - Problem 14.1 The NMR spectrum of recorded on a ...Ch. 14 - Prob. 14.2PCh. 14 - How many NMR signals does each compound show?
a....Ch. 14 - How many 1H NMR signals does each...Ch. 14 - How many 1H NMR signals does each compound give?...Ch. 14 - Label the protons in each highlighted CH2 group as...Ch. 14 - How many 1H NMR signals would you expect for each...Ch. 14 - Prob. 14.8PCh. 14 - For each compound, first label each different type...Ch. 14 - Label each statement as True or False. a. When a...
Ch. 14 - Prob. 14.11PCh. 14 - Problem 14.12 Which compound give a NMR spectrum...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Problem 14.18 Describe the NMR spectrum of each...Ch. 14 - Problem 14.19 Draw a splitting diagram for in ,...Ch. 14 - Problem 14.20 Identify A and B, isomers of...Ch. 14 - Problem 14.21 How many signals are present in the ...Ch. 14 - Problem 14.22 What protons in alcohol A give rise...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 -
Problem 14.24 Propose a structure for a compound...Ch. 14 - Problem 14.25 Propose a structure for a compound...Ch. 14 - Problem 14.26. Identify products A and B from the...Ch. 14 - Problem 14.27 How many lines are observed in the ...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Problem 14.29 Esters of chrysanthemic acid are...Ch. 14 - Prob. 14.30PCh. 14 - Problem 14.31 Identify the carbon atoms that give...Ch. 14 - Problem 14.32 A compound of molecular formula ...Ch. 14 - Problem 14.33 Draw the structure of a compound of...Ch. 14 - 14.34 (a) How many NMR signals does each of the...Ch. 14 - 14.35 (a) How many NMR signals does each compound...Ch. 14 - Prob. 14.36PCh. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - 14.39 What effect does increasing the operating...Ch. 14 - Prob. 14.40PCh. 14 - 14.41 How could you use chemical shift and...Ch. 14 - Prob. 14.42PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - 14.48 How many NMR signals does each compound...Ch. 14 - 14.49 Rank the highlighted carbon atoms in each...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.52 Answer the following questions about each of...Ch. 14 - 14.53 Propose a structure consistent with each set...Ch. 14 - 14.54 Identify the structures of isomers A and B...Ch. 14 - 14.55 Reaction of with affords compound W,...Ch. 14 - 14.56 Treatment of with , followed by aqueous
...Ch. 14 - 14.57 Compound C has a molecular ion in its mass...Ch. 14 - 14.58 As we will learn in Chapter 20, reaction of ...Ch. 14 - 14.59 Identify the structures of isomers E and F...Ch. 14 - 14.59 Identify the structures of isomers H and I...Ch. 14 - 14.61 Propose a structure consistent with each set...Ch. 14 - 14.62 Reaction of with , followed by treatment...Ch. 14 - Reaction of aldehyde D with amino alcohol E in the...Ch. 14 - 14.64 Propose a structure consistent with each set...Ch. 14 - 14.65 In the presence of a small amount of acid, a...Ch. 14 - 14.66 Treatment of with affords two products (M...Ch. 14 - 14.67 Compound O has molecular formula and shows...Ch. 14 - 14.68 Compound P has molecular formula . Deduce...Ch. 14 - 14.69 Treatment of with strong base followed by ...Ch. 14 - 14.70 When -bromo--dimethylbutane is treated with...Ch. 14 - 14.71 Propose a structure consistent with each set...Ch. 14 - 14.72 Reaction of unknown A with forms...Ch. 14 - Prob. 14.73PCh. 14 - 14.74 -Annulene shows two signals in its ...Ch. 14 - 14.75 Explain why the spectrum of-methylbutan--ol...Ch. 14 - 14.76 Because has an odd mass number, nuclei...Ch. 14 - 14.77 Cyclohex--enone has two protons on its...
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- Which compounds give a 'H NMR spectrum with two signals in a ratio of 2:3? a. CH;CH,CI b. CH;CH2CH3 c. CH;CH2OCH2CH3 d. CH;OCH,CH,OCH3arrow_forwardHow many signals are observed for the following molecule 4.1. In its 'H NMR spectrum? 4.2. In its 1³C NMR spectrum? 4.arrow_forwardHow many lines are observed in the 13C NMR spectrum of each attached compound ?arrow_forward
- 30. Predict the chemical shifts for the signals in the 'H-NMR spectrum of each of the following compounds. a. b.arrow_forward16.64 Which of the two 13C NMR spectra below corresponds to chlorocyclohexane and which corresponds to iodocyclohexane? Explain. 200 150 100 50 200 150 100 50 Chemical shift (ppm) Chemical shift (ppm)arrow_forwardExplain why the answer is A regarding to H-NMR belowarrow_forward
- Draw the structure of the ether that has a chemical formula C8H10O2, has a molecular ion peak at 138, and is represented by the IR, 'H NMR, and 13 C NMR belowarrow_forwardDraw all constitutional isomers of molecular formula CgH,Cl2. a. How many signals does each isomer exhibit in its 'H NMR spectrum? b. How many lines does each isomer exhibit in its 18C NMR spectrum? c. When only the number of signals in both 'H and 19C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?arrow_forwardB.19 What major IR absorptions are present above 1500 cm ¹ for each compound? a. b. C. d. OH OHarrow_forward
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY