Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 5, Problem 5.11P
The structure of 1,2-propadiene (allene) is shown to the right.
- (a) Predict all approximate bond angles in this molecule.
- (b) State the orbital hybridization of each carbon.
- (c) Explain the three-dimensional geometry of allene in terms of the orbitals used.
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Describe the molecular geometry and hybridization of the N, P, or S atoms in each of the following compounds.
(a) H3PO4, phosphoric acid, used in cola soft drinks
(b) NH4NO3, ammonium nitrate, a fertilizer and explosive
(c) S2Cl2, disulfur dichloride, used in vulcanizing rubber
(d) K4[O3POPO3], potassium pyrophosphate, an ingredient in some toothpastes
Chapter 5 Solutions
Organic Chemistry
Ch. 5.1 - Calculate the index of hydrogen deficiency for...Ch. 5.1 - Prob. 5.2PCh. 5.2 - Write the IUPAC name of each alkene. (a) (b)Ch. 5.2 - Prob. 5.4PCh. 5.2 - Prob. 5.5PCh. 5.2 - Prob. 5.6PCh. 5.2 - Prob. 5.7PCh. 5.2 - Prob. 5.8PCh. 5 - Predict all approximate bond angles about each...Ch. 5 - Prob. 5.10P
Ch. 5 - The structure of 1,2-propadiene (allene) is shown...Ch. 5 - Prob. 5.12PCh. 5 - Draw structural formulas for these alkenes. (a)...Ch. 5 - Name these alkenes and cycloalkenes.Ch. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - For each molecule that shows cis, trans isomerism,...Ch. 5 - -Ocimene, a triene found in the fragrance of...Ch. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Measure the CH3,CH3 distance in the...Ch. 5 - Prob. 5.26PCh. 5 - Measure the CCC and CCH bond angles in the...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Pyrethrin II and pyrethrosin are two natural...Ch. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Bromine adds to cis- and trans-2-butene to give...
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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
- Describe the molecular geometry and hybridization of the N, P, or S atoms in each of the following compounds.(a) H3PO4, phosphoric acid, used in cola soft drinks(b) NH4NO3, ammonium nitrate, a fertilizer and explosive(c) S2Cl2, disulfur dichloride, used in vulcanizing rubber(d) K4[O3POPO3], potassium pyrophosphate, an ingredient in some toothpastesarrow_forwardIdentify any carbon atoms that change hybridization and the change in hybridization during the reactions in (a) 2-butene reacts with chlorine.(b) benzene burns in air.arrow_forward(a) Describe the hybridization of the central atom of a molecule with a see-saw shape. (b) Describe the hybridization of the central atom of a molecule with a trigonal planar shape. (c) Describe the hybridization of the central atom of a molecule with a trigonal bipyramidal shape.arrow_forward
- For each statement, indicate whether it is true or false. (a) The greater the orbital overlap in a bond, the weaker the bond. [b] The greater the orbital overlap in a bond, the shorter the bond. [c] To create a hybrid orbital, you could use the s orbital on one atom with a p orbital on another atom. [d] Nonbonding electron pairs cannot occupy a hybrid orbital.arrow_forward(a) Draw Lewis structures for ethane 1C2H62, ethylene1C2H42, and acetylene 1C2H22. (b) What is the hybridizationof the carbon atoms in each molecule? (c) Predict whichmolecules, if any, are planar. (d) How many s and p bondsare there in each molecule?arrow_forwardDraw a Lewis electron dot diagram for each of the follow- ing molecules and ions. Formulate the hybridization for the central atom in each case and give the molecular geometry. (a) BF3 (b) BH4- (c) PH3 (d) CS2 (e) CH3+arrow_forward
- Organic compounds (a) A simple molecule with alternating single and double bonds is buta-1,3-diene. (i) Draw its skeletal structure. (ii) Write its molecular formula and empirical formula. (iii) How many carbon atoms have sp2 hybridization in buta-1,3-diene?arrow_forward(a) Sketch the molecular orbitals of the H2- ion and draw itsenergy-level diagram. (b) Write the electron configuration ofthe ion in terms of its MOs. (c) Calculate the bond order inH2-. (d) Suppose that the ion is excited by light, so that anelectron moves from a lower-energy to a higher-energy molecularorbital. Would you expect the excited-state H2- ion to bestable? (e) Which of the following statements about part (d) is correct: (i) The light excites an electron from a bonding orbitalto an antibonding orbital, (ii) The light excites an electronfrom an antibonding orbital to a bonding orbital, or (iii)In the excited state there are more bonding electrons thanantibonding electrons?arrow_forwardButadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths: (a) Predict the bond angles around each of the carbon atoms and sketch the molecule. (b) From left to right, what is the hybridization of each carbon atom in butadiene? (c) The middle C—C bond length in butadiene (1.48 Å) is a little shorter than the average C—C single bond length (1.54 Å). Does this imply that the middle C—C bond in butadiene is weaker or stronger than the average C—C single bond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might support the shorter middle C—C bond.arrow_forward
- The sulfate ion can be represented with four S-O bonds or with two S-O and two So=O bonds.(a) Which representation is better from the standpoint of formal charges?(b) What is the shape of the sulfate ion, and what hybrid orbitals of S are postulated for the σ bonding?(c) In view of the answer to part (b), what orbitals of S must be used for the π bonds? What orbitals of O?(d) Draw a diagram to show how one atomic orbital from S and one from O overlap to form a π bond.arrow_forward(a) Write a single Lewis structure for SO3 , and determine the hybridization at the S atom. (b) Are there other equivalent Lewis structures for the molecule? (c) Would you expect SO3 to exhibit delocalized π bonding?arrow_forwardA useful solvent that will dissolve salts as well as organic compounds is the compound acetonitrile, H3CCN. It is present in paint strippers.(a) Write the Lewis structure for acetonitrile, and indicate the direction of the dipole moment in the molecule.(b) Identify the hybrid orbitals used by the carbon atoms in the molecule to form σ bonds.(c) Describe the atomic orbitals that form the π bonds in the molecule. Note that it is not necessary to hybridize the nitrogen atom.arrow_forward
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