Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 1.14, Problem 30P
Which of the bonds in a carbon–oxygen double bond has more effective orbital–orbital overlap, the σ bond or the π bond?
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What does the following figure represent?
the overlap of two 1s orbitals to form a pi bond
the overlap of a 1s orbital and a 2p orbital to form a sigma bond
the overlap of a 1s orbital and a 2p orbital to form a pi bond
the overlap of two 2p orbitals to form a sigma bond
the overlap of two 2p orbitals to form a pi bond
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For acetaldehyde (CH3CHO) write the
Lewis structure. Write the hybridization
and geometry of each carbon. Draw its
3D structure and write the bond angles
(approximately).
The concept of valence-shell electron-pair repulsion
(VSEPR) is presented in introductory organic chemistry
as a way to predict molecular geometries. The idea be-
hind VSEPR is that areas of electron density repel each
other so that the geometry of bonds and/or lone pairs
of electrons around any one atom places these areas as
far apart as possible. For four areas of electron density,
a tetrahedral geometry is predicted. For three areas of
electron density, a trigonal planar geometry is predicted.
Two areas of electron density lead to a linear geometry.
VSEPR is simply a predictive tool, but in some
cases, it gives an incorrect prediction. In these
instances, additional insights into bonding are
necessary, such as resonance. Interestingly, several
important situations are critical to biochemistry where
VSEPR breaks down. Two examples are shown here.
:O:
CH3
H,N
H3N
CH3 H
:0:
:0:
Histidine
The circled nitrogen atoms are predicted by VSEPR
to be tetrahedral in geometry because each…
Chapter 1 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.2 - Prob. 2PCh. 1.2 - How many valence electrons do chlorine, bromine,...Ch. 1.2 - Look at the relative positions of each pair of...Ch. 1.3 - a. Find potassium (K) in the periodic table and...Ch. 1.3 - Which bond is more polar?Ch. 1.3 - Which of the following has a. the most polar bond?...Ch. 1.3 - Use the symbols + and to show the direction of...Ch. 1.3 - After examining the potential maps for LiH, HF,...Ch. 1.4 - An atom with a formal charge does not necessarily...
Ch. 1.4 - Prob. 12PCh. 1.4 - a. Draw two Lewis structures for C2H6O. b. Draw...Ch. 1.4 - Draw the lone-pair electrons that are not shown in...Ch. 1.4 - Prob. 16PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 18PCh. 1.7 - What orbitals are used to form the 10 sigma bonds...Ch. 1.9 - Put a number in each of the blanks: a. ___ s...Ch. 1.11 - Predict the approximate bond angles in a. the...Ch. 1.11 - According to the potential map for the ammonium...Ch. 1.12 - Prob. 25PCh. 1.13 - a. Predict the relative lengths and strengths of...Ch. 1.13 - Prob. 28PCh. 1.14 - Which of the bonds in a carbonoxygen double bond...Ch. 1.14 - Caffeine is a natural insecticide, found in the...Ch. 1.14 - a. What is the hybridization of each of the carbon...Ch. 1.14 - Prob. 33PCh. 1.14 - Describe the orbitals used in bonding and the bond...Ch. 1.15 - Account for the difference in the shape and color...Ch. 1.15 - Which of the following molecules would you expect...Ch. 1 - Draw a Lewis structure for each of the following...Ch. 1 - Prob. 38PCh. 1 - What is the hybridization of all the atoms (other...Ch. 1 - Prob. 40PCh. 1 - Draw the condensed structure of a compound that...Ch. 1 - Prob. 42PCh. 1 - Prob. 43PCh. 1 - Draw a Lewis structure for each of the following...Ch. 1 - Prob. 45PCh. 1 - List the bonds in order from most polar to least...Ch. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Write the Kekul structure for each of the...Ch. 1 - Assign the missing formal charges.Ch. 1 - Predict the approximate bond angles for the...Ch. 1 - Prob. 51PCh. 1 - a. Which of the indicated bonds in each compound...Ch. 1 - In which orbitals are the lone pairs in nicotine?...Ch. 1 - Draw the missing lone-pair electrons and assign...Ch. 1 - Rank the following compounds from highest dipole...Ch. 1 - Prob. 56PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 58PCh. 1 - Sodium methoxide (CH3ONa) has both ionic and...Ch. 1 - a. Why is a H 8 H bond (0.74 ) shorter than a C 8...Ch. 1 - Which compound has a larger dipole moment, CHCl3...Ch. 1 - Which compound has a longer C 8 Cl bond?Ch. 1 - Prob. 63PCh. 1 - The following compound has two isomers. One isomer...
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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
- Methylcyanoacrylate is the active ingredient in super glues. Its Lewis structure is (a) Give values for the three bond angles indicated. (b) Indicate the most polar bond in the molecule. (c) Circle the shortest carbon-oxygen bond. (d) Circle the shortest carbon-carbon bond.arrow_forwardAccording to the valence bond theory, which kind of orbitals overlap to form the P-Cl bond?arrow_forwardHow does hybridization of atomic orbitals occur in carbon atoms?arrow_forward
- What is the molecular geometry for the bromate ion, BrO3-?arrow_forwardBonding in the chlorine molecule can be explained by the valence bond theory in terms of an overlap between The 1s orbital of a chlorine atom and the 1s orbital of the other chlorine atom The 3p orbital of a chlorine atom and the 3p orbital of the other chlorine atom 2p orbital of chlorine atom and 2p of other chlorine atom The 2s orbital of chlorine atom and 2s of other chlorine The 3s orbital of chlorine and 3s of other chlorine atomarrow_forwardDescribe the hybrid orbitals used by the carbon atom inN=C-Cl. Predict the geometry of the molecule.arrow_forward
- Predict the geometry and bond angles around atom A for molecules with the general formulas AB4, AB3E, and AB2E2, where B represents another atom and E represents an electron pair.arrow_forwardPart A Benzene is an organic chemical compound with the molecular formula C6H6. In the benzene molecule, carbon atoms form a ring with alternating single and double bonds connecting them. Thus, each individual carbon atom forms one o bond with another carbon atom and one o and one bond with another carbon atom. Each carbon atom also forms one o bond with a hydrogen atom. H H sp³-sp³ H Identify which types of orbitals overlap to form the bonds between the atoms in a benzene molecule. Drag the appropriate labels to their respective targets. ► View Available Hint(s) sp-sp sp² - sp² р-р Bonds formed Carbon-carbon o bond Carbon-carbon 7 bond H-C Carbon-hydrogen o bond C=C C-H H Type of orbitals involved P Pearson Reset Helparrow_forwardIt is common for carbon to form a carbon-carbon double bond, however silicon-silicon double bond is less common. Use valence bond theory to account for this.arrow_forward
- Draw the Lewis structure for chloroform, CHCl3. What are its electron-pair and molecular geometries? What orbitals on C, H, and Cl overlap to form bonds involving these elements?arrow_forwardWhen two carbons having different hybridization are bonded together, the C–C bond contains a slight dipole. In a Csp2–Csp3 bond, what is the direction of the dipole? Which carbon is considered more electronegative?arrow_forwardFor the carbonate ion, CO32−,CO32−, draw all of the resonance structures. Identify which orbitals overlap to create each bond.arrow_forward
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