Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 1, Problem 75P
Anacin is an over-the-counter pain reliever that contains aspirin and caffeine. Answer the following
questions about each compound.
a. What is the molecular formula?
b. How many lone pairs are present on heteroatoms?
c. Label the hybridisation state of each carbon.
d. Draw three additional resonance structures.
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Anacin is an over-the-counter pain reliever that contains aspirin and caffeine. Answer the following questions about each compound.
a.What is the molecular formula?
b. How many lone pairs are present on heteroatoms?
c. Label the hybridization state of each carbon.
d. Draw three additional resonance structures.
Answer the following questions about octocrylene, a common sunscreen component.
a. What is the hybridization of each C atom?
b. How many lone pairs does octocrylene contain?
c. What is the geometry around each C atom?
d. Draw two additional resonance structures.
e. Label all polar bonds.
Answer the following questions about compound A.
a. Label the shortest C-C single bond.
b. Label the longest C-C single bond.
c. Considering all the bonds, label the shortest C-C bond.
d. Label the weakest C-C bond.
e. Label the strongest C-H bond.
f. Explain why bond (1) and bond (2) are different in length, even though they are both C-C
single bonds.
(2)
Chapter 1 Solutions
Organic Chemistry (6th Edition)
Ch. 1.1 - While the most common isotope of nitrogen has a...Ch. 1.2 - Label each bond in the following compounds as...Ch. 1.3 - Draw a valid Lewis structure for each species. a....Ch. 1.3 - Prob. 9PCh. 1.4 - Draw Lewis structures for each molecular formula....Ch. 1.6 - Classify each pair of compounds as isomers or...Ch. 1.6 - Prob. 12PCh. 1.6 - Prob. 13PCh. 1.6 - Prob. 14PCh. 1.6 - Prob. 16P
Ch. 1.6 - Prob. 17PCh. 1.7 - Prob. 18PCh. 1.7 - Prob. 19PCh. 1.7 - Using the principles of VSEPR theory, you can...Ch. 1.8 - Convert each condensed formula to a Lewis...Ch. 1.8 - Prob. 22PCh. 1.8 - Prob. 23PCh. 1.8 - Convert each skeletal structure to a complete...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 and atom in the...Ch. 1 - Prob. 44PCh. 1 - Prob. 46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 52PCh. 1 - Prob. 53PCh. 1 - Prob. 54PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 65PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 68PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 74PCh. 1 - Anacin is an over-the-counter pain reliever that...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. 83PCh. 1 - Prob. 84PCh. 1 - Prob. 85PCh. 1 - Prob. 86PCh. 1 - Prob. 87PCh. 1 - Prob. 88P
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- 3. The following shows all resonance structures for the following molecule. a. Draw in all implied lone pairs. b. Draw in curved arrows that show the flow of electrons, making sure the arrows show the precise starting point and destination of the electrons. Label each arrow as: lp →→→л (p=lone pair) c. d. Rank the resonance structures from most stable to least based on the number of formal charges and atoms that lack an octet of electrons. ol-of-o. B A D d-d-d-o E C F Garrow_forward2. Draw a Lewis structure for each molecule or ion below. Draw any resonance structures. Determine the form al charges on atoms in each of your resonance structures. Based on this, determine which resonance structure(s) are most im portant. Circle the most important contributor(s) to the resonance hybrid. If they are all equivalent, circle them all. a. NO, b. COFCIarrow_forwardTrue or False? Circle your answer.a. A resonance hybrid is a structure with equal contribution from each possible resonance structure.True Falseb. Localized electrons do not participate in resonance.True Falsearrow_forward
- 1. Draw all resonance structures for each of the following molecules or ions. Be sure to include curved arrows that indicate which pair of electrons are shifted in going (flowing) from one resonance structure to the next. a. b. C. 0-2,000arrow_forwardB. On top of the given structure draw the molecular dipole moment. CI F Brarrow_forwardStalevo is the trade name for a medication used for Parkinson's disease, which contains L-dopa, carbidopa, and entacapone. a. Draw a Lewis structure for entacapone. b. Which C–C bond in entacapone is the longest? c. Which C–C single bond is the shortest? d. Which C–N bond is the longest? e Which C–N bond is the shortest? f. Use curved arrows to draw a resonance structure that is an equal contributor to the resonance hybrid. g. Use curved arrows to draw a resonance structure that is a minor contributor to the resonance hybrid.arrow_forward
- Creatine is a dietary supplement used by some athletes to boost their athletic performance. NH2 H2N' `N' creatine a. Draw in all lone pairs in creatine. b. Draw two additional resonance structures shwing all lone pairs and formal charges.arrow_forwardConsidering the structure on the far left as the original resonance structure, which of the subsequent resonance structures (A-D) is implausible. Explain why you believe the resonance structure to be implausible.arrow_forwardDraw a second resonance structure for each ion. Then, draw the resonance hybrid.arrow_forward
- Follow the curved arrows to draw a second resonance structure for eachspecies.arrow_forwardThree resonance structures of the given anion are possible. One is given, but it is incomplete. Complete the given structure by adding nonbonding electrons and formal charges. Draw the two remaining resonance structures (in any order), including nonbonding electrons and formal charges. Omit curved arrows. Structure A: Complete the resonance structure. Structure B: Draw a resonance structure. Select Draw Rings More Erase Select Draw Rings More Erase C MacBookarrow_forwardDraw a resonance structure that shifts a pi bond to a new position. Include all hydrogen atoms and lone pairs in your structure.arrow_forward
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