Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 1, Problem 1.16P
Interpretation Introduction
(a)
Interpretation: The second resonance structure for A is to be drawn with the help of curved arrows.
Concept Introduction: Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.
Interpretation Introduction
(b)
Interpretation: The second resonance structure for A is to be drawn with the help of curved arrows.
Concept Introduction: Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.
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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.
Draw all reasonable resonance structures.
b)
c)
H₂N-
OH
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.
Chapter 1 Solutions
Organic Chemistry
Ch. 1 - While the most common isotope of nitrogen has a...Ch. 1 - Label each bond in the following compounds as...Ch. 1 - How many covalent bonds are predicted for each...Ch. 1 - Draw a valid Lewis structure for each species. a....Ch. 1 - Draw an acceptable Lewis structure for each...Ch. 1 - Prob. 1.6PCh. 1 - Draw a Lewis structure for each ion. a. CH3Ob....Ch. 1 - Prob. 1.8PCh. 1 - Draw Lewis structures for each molecular formula....Ch. 1 - Classify each pair of compounds as isomers or...
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Draw a second resonance structure for each species...Ch. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Using the principles of VSEPR theory, you can...Ch. 1 - Convert each condensed formula to a Lewis...Ch. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - What is the molecular formula of quinine, the...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - The unmistakable odor of a freshly cut cucumber is...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each and atom in the...Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - 1.58 Predict the geometry around each highlighted...Ch. 1 - Prob. 1.59PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 1.65PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Prob. 1.68PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 1.71PCh. 1 - Anacin is an over-the-counter pain reliever that...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.74PCh. 1 - 1.75 The principles of this chapter can be...Ch. 1 -
a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.83PCh. 1 - Prob. 1.84PCh. 1 - Prob. 1.85P
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- 11) Which resonance structure is of a compound different than the others? dora a) و کا b) d) CH₂ NHarrow_forward(a) Draw a second resonance structure for A. (b) Why can't a second resonance structure be drawn for B?arrow_forwardChemistry (a) Write three more resonance structures for each of compounds 1 and 2. (b) In each of compounds 1 and 2, determine which resonance structure contributes the most and explain your answer. (c) Are the 3/4 structures resonance structures or different compounds? Same question for 5/6 structures. Explain your answers.arrow_forward
- (a) Draw all resonance contributors of the following ion. In drawing each additional resonance structure, use curved arrows to indicate which pairs of electrons are being shifted. (b) Draw the resonance hybrid. (c) Which c–C bond is the longest?arrow_forwardWhich of the following species is a valid resonance structure of A? Usecurved arrows to show how A is converted to any valid resonancestructure. When a compound is not a valid resonance structure of A,explain why not.arrow_forward(a) Draw a second resonance structure for A. (b) Why can’t a second resonance structure be drawn for B?arrow_forward
- Draw 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_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_forwardDraw Lewis structures and any contributing resonance structures for each structure below. Use the proper type of arrow to indicate that they are resonance structures. In which structure is resonance more important? (a) H2SO3 (b) (HSO3)^1- (c) (SO3)^2-arrow_forward
- please draw it out and explain how to do it. i would like to learnarrow_forwardDraw 3 resonance structures of CNO- (connected in that order) and rank them in terms of stability.arrow_forwardLinoleic acid is an essential fatty acid found in many veg-etable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the c is orientation around its two dou-ble bonds, where R1and R2 represent two different groups thatform the rest of the molecule. (a) How many different compounds are possible, changing onlythe cis-trans arrangements around these two double bonds?(b) How many are possible for a similar compound with three double bonds?arrow_forward
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