Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 2, Problem 19PP
Interpretation Introduction
Interpretation:
The resonance structures for the given compound are to be drawn that results from moving the electrons as indicated. Also, all formal charges are to be included.
Concept introduction:
If it is possible to draw more than one Lewis structure for a molecule or ion, then such structures are said to be in resonance.
Resonance structure is the name given to the individual Lewis structures.
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2. On the first drawing on the left for each structure below, draw the electron pushing arrows needed to
produce the resonance structure on the right. The structures are bond-line; you need to draw the
implied lone pair electrons that participate in resonance.
(b)
(a)
Ⓒ
PRACTICE PROBLEM 2.12 Write bond-line structural formulas for (a) two primary alcohols, (b) a secondary alcohol,
and (e) a tertiary alcohol-all having the molecular formula C,H190.
• PRACTICE PROBLEM 2.13 One way of naming alcohols is to name the alkyl group that is attached to the -OH and
add the word alcohol. Write bond-line formulas for (a) propyl alcohol and (b) isopropyl
alcohol.
Consider compounds A–D, which contain both a heteroatom and a double bond.
(a) For which compounds are no additional Lewis structures possible?
(b) When two or more Lewis structures can be drawn, draw all additional resonance structures.
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - Practice Problem 2.1
Propose structures for two...Ch. 2 - Prob. 2PPCh. 2 - Prob. 3PPCh. 2 - Prob. 4PPCh. 2 - Prob. 5PPCh. 2 - Practice Problem 2.6
Using a three-dimensional...Ch. 2 - Practice Problem 2.7
Trichloromethane (, also...Ch. 2 - Prob. 8PPCh. 2 - Prob. 9PPCh. 2 - Practice Problem 2.10
Write bond-line structural...
Ch. 2 - Practice Problem 2.11 Although we shall discuss...Ch. 2 - Practice Problem 2.12 Write bond-line structural...Ch. 2 - Prob. 13PPCh. 2 - Practice Problem 2.14
One way of naming ethers is...Ch. 2 - Practice Problem 2.15 Eugenol is the main...Ch. 2 - Practice Problem 2.16
One way of naming amines is...Ch. 2 - Practice Problem 2.17 Which amines in Practice...Ch. 2 - Prob. 18PPCh. 2 - Prob. 19PPCh. 2 - Practice Problem 2.20
Write bond-line formulas for...Ch. 2 - Practice Problem 2.21
Write bond-line formulas for...Ch. 2 - Practice Problem 2.22
Write bond-line formulas for...Ch. 2 - Prob. 23PPCh. 2 - Practice Problem 2.24 Write another resonance...Ch. 2 - Prob. 25PPCh. 2 - Practice Problem 2.26
Which compound would you...Ch. 2 - Practice Problem 2.27 Arrange the following...Ch. 2 - Prob. 28PPCh. 2 - Prob. 29PCh. 2 - Identify all of the functional groups in each of...Ch. 2 - 2.31 There are four alkyl bromides with the...Ch. 2 - Prob. 32PCh. 2 - Classify the following alcohols as primary,...Ch. 2 - 2.34 Classify the following amines as primary,...Ch. 2 - Prob. 35PCh. 2 - Identify all of the functional groups in Crixivan,...Ch. 2 - 2.37 Identify all of the functional groups in...Ch. 2 - 2.38 (a) Indicate the hydrophobic and hydrophilic...Ch. 2 - Hydrogen fluoride has a dipole moment of 1.83 D;...Ch. 2 - 2.40 Why does one expect the cis isomer of an...Ch. 2 - Prob. 41PCh. 2 - Prob. 42PCh. 2 - Prob. 43PCh. 2 - 2.44 Consider each of the following molecules in...Ch. 2 - True or false: For a molecule to be polar, the...Ch. 2 - 2.46 Which compound in each of the following...Ch. 2 - Prob. 47PCh. 2 - The IR spectrum of propanoic acid (Fig. 2.16)...Ch. 2 - Prob. 49PCh. 2 - Write structural formulas for four compounds with...Ch. 2 - There are four amides with the formula C3H7NO. (a)...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - 2.56 Compound C is asymmetric, has molecular...Ch. 2 - 2.57 Examine the diagram showing an -helical...Ch. 2 - Prob. 1LGPCh. 2 - Prob. 2LGPCh. 2 - Prob. 3LGPCh. 2 - Consider the molecular formula C4H8O2. Predict...Ch. 2 - Consider the molecular formula C4H8O2. If any of...Ch. 2 - Prob. 6LGPCh. 2 - Consider the molecular formula.
7. Pick five...Ch. 2 - Prob. 8LGP
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- The curved arrow notation introduced in Section 1.6B is a powerfulmethod used by organic chemists to show the movement of electronsnot only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons,following the curved arrows illustrates what bonds are broken andformed in a reaction. Consider the following three-step process. (a) Addcurved arrows in Step [1] to show the movement of electrons. (b) Use thecurved arrows drawn in Step [2] to identify the structure of X. X isconverted in Step [3] to phenol and HCl.arrow_forwardPlease don't provide handwritten solution ...arrow_forwardThe curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forward
- PRACTICE PROBLEM 2.25 The compounds in each part below have the same (or similar) molecular weights. Which compound in each part would you expect to have the higher boiling point? Éxplain your answers. OH or HO. (a) (c) но OH or (b) (CHa),N orarrow_forwardThe curved arrow notation introduced in Section 1.6 is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions. Since each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forwardThe curved arrow notation introduced in Section 1.6 is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions. Since each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forward
- Problem Draw Lewis structures for the following:(a) Ethylene (C2H4), the most important reactant in the manufacture of polymers(b) Nitrogen (N2), the most abundant atmospheric gasPlan We show the structure resulting from steps 1 to 4: placing the atoms, counting the total valence electrons, making single bonds, and distributing the remaining valence electrons in pairs to attain octets. Then we continue with step 5, if needed.arrow_forwardPlease don't provide handwritten solution.....arrow_forwardDraw all resonance contributors for each of the following molecules or ions. Be sure to include the curved arrows that indicate which pairs of electrons are shifted in going from one resonance structure to the next. (a) CH3NO2 (b) CH, CO, (c) CH CHCHCH2 (the ion has two C-C single bonds) (d) C5H5N (a ring is formed by the C and N atoms, and each H is bonded to a C atom) (e) C4H5N (a ring is formed by the C and N atoms, and the N is bonded to one H atom, and each C atom is bonded to one H atom)arrow_forward
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