Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 1, Problem 1.30P
The unmistakable odor of a freshly cut cucumber is largely due to cucumber
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The unmistakable odor of a freshly cut cucumber is largely due to cucumber aldehyde. (a) How
many sp² hybridized carbon atoms does cucumber aldehyde contain? (b) What is the hybridization
of the O atom? (c) What orbitals are used to form the carbon-oxygen double bond? (d) How many
o bonds does cucumber aldehyde contain? (e) How many bonds does it contain?
and
-gle 120°
M
Sp²
hundre
bond and I doule
cucumber aldehyde
H
H
genistein
HO,
H
H
: ОН
HO,
H
(a) Is the hybridization of each C in the right-most ring the same? Explain.
(b) Is the hybridization of the O atoms in/on the center ring the same as that of the O atoms in the OH
groups? Explain.
(c) How many carbon-oxygen o-bonds are there in genistein? How many carbon-oxygen n-bonds?
(d) Do all the lone pairs on the oxygens occupy the same type of hybrid orbital? Explain by labeling
the hybridization of each oxygen atom in genistein.
Draw the line-bond structure of oleic acid (cis-9-octadecenoic acid), CH3(CH2)7CH=CH(CH2)7COOH, at physiological pH. You do not need to draw hydrogen atoms attached to carbon atoms.
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Linoleic acid is an essential fatty acid found in many vegetable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the cis orientation around its two double bonds, where R1 and R2 represent two different groups that form the rest of the molecule. (a) How many different compounds are possible, changing only the cis-trans arrangements around these two double bonds? (b) How many are possible for a similar compound with three double bonds?arrow_forwardMethyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?arrow_forwardAn acyclic molecule has the molecular formula C8H14. How many pi bonds does it contain?arrow_forward
- (a) How is each N atom in quinine, an effective antimalarial drug that reduces fever, hybridized? (b) In what type of orbital does the lone pair on each N reside?arrow_forwardThe unmistakable odor of a freshly cut cucumber is largely due to cucumber aldehyde. (a) How many sp2 hybridizedcarbon atoms does cucumber aldehyde contain? (b) What is the hybridization of the O atom? (c) What orbitals are used toform the carbon–oxygen double bond? (d) How many s bonds does cucumber aldehyde contain? (e) How many p bondsdoes it contain?arrow_forward7 The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.arrow_forward
- The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?arrow_forwardThe drawing below shows the overlap of two hybrid orbitalsto form a bond in a hydrocarbon. (a) Which of the followingtypes of bonds is being formed: (i) C¬C σ, (ii) C¬C π,or (iii) C¬H σ? (b) Which of the following could be theidentity of the hydrocarbon: (i) CH4, (ii) C2H6, (iii) C2H4, or(iv) C2H2?arrow_forwardDimethyl sulfoxide (DMSO) has been used as an anti-inflammatory rub for racehorses. DMSO and acetone appear to have similar structures, but the C“O carbon atom in acetone is planar, while the S“O sulfur atom in DMSO ispyramidal. Draw Lewis structures for DMSO and acetone, predict the hybridizations and explain these observations.arrow_forward
- 7) Which orbitals overlap to form the sigma and pi bonds in the following structure of carbon dioxide?arrow_forwardTwo useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCI) and chloroethane (CH;CH;CI). Vinyl chloride is the starting material used to prepare poly (vinyl chloride), a plastic used in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C- Cl bond of vinyl chloride stronger than the C– CIl bond in chloroethane.arrow_forwardGive the (a) bond order and (b) hybridization state of each carbon atom of propadiene, H2CCCH2.arrow_forward
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