CHEMISTRY-MASTERINGCHEMISTRY W/ETEXT
8th Edition
ISBN: 9780135204634
Author: Robinson
Publisher: PEARSON
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Chapter 8, Problem 8.29CP
Three of the following molecular models have a tetrahedral central atom, and one does not. Which is the odd one? (There maybe a “hidden” atom directly behind a visible atom in some cases.)
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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any.
If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers).
If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products.
If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a
NaBH4 reduction?
1. Give stereochemical (Fischer projection) formulas for all (but no extras) the
stereoisomers that could theoretically form during the reduction of
a. the carbonyl group of 2-methyl-3--pentanone
b. both carbonyl groups of 2,4-pentanedione (careful!)
2. Predict the products of the reduction of O=CCH2CH2CH2C=O with
a. LiAlH4
b. NaBH4
CH3
OH
Chapter 8 Solutions
CHEMISTRY-MASTERINGCHEMISTRY W/ETEXT
Ch. 8 - Prob. 8.1PCh. 8 - What is the number and geometric arrangement of...Ch. 8 - PRACTICE 8.3 Acetic acid, CH3CO2H , is the main...Ch. 8 - APPLY 8.4 Benzene, C6H6 , is a cyclic molecule in...Ch. 8 - PRACTICE 8.5 Identify the orbitals that overlap to...Ch. 8 - APPLY 8.6 Describe the bonding in propane, C3H8 ,...Ch. 8 - PRACTICE 8.7 Describe the hybridization of the...Ch. 8 - Describe the hybridization of each carbon atom in...Ch. 8 - Which orbitals overlap to form the sigma and pi...Ch. 8 - APPLY 8.10 Describe the hybridization of the...
Ch. 8 - Prob. 8.11PCh. 8 - Conceptual APPLY 8.12 Match the following...Ch. 8 - Prob. 8.13PCh. 8 - Prob. 8.14ACh. 8 - Prob. 8.15PCh. 8 - Prob. 8.16ACh. 8 - Prob. 8.17ACh. 8 - Prob. 8.18ACh. 8 - The B2 molecule has a MO diagram similar to that...Ch. 8 - Prob. 8.20ACh. 8 - PRACTICE 8.23 Draw two resonance structures for...Ch. 8 - APPLY 8.24 Draw two resonance structures for the...Ch. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - Caffeine is the most widely used stimulant...Ch. 8 - Prob. 8.26PCh. 8 - What is the geometry around the central atom in...Ch. 8 - What is the geometry around the central atom in...Ch. 8 - Three of the following molecular models have a...Ch. 8 - Identify each of the following sets of hybrid...Ch. 8 - The VSEPR model is a simple predictive tool that...Ch. 8 - The following ball-and-stick molecular model is a...Ch. 8 - The following ball-and-stick molecular model is a...Ch. 8 - Prob. 8.34CPCh. 8 - The dipole moment of methanol is =1.70D . Use...Ch. 8 - Methylarnine, CH3NH2 , is responsible for the odor...Ch. 8 - Prob. 8.37CPCh. 8 - Prob. 8.38SPCh. 8 - What shape do you expect for molecules that meet...Ch. 8 - How many charge clouds are there around the...Ch. 8 - Prob. 8.41SPCh. 8 - What shape do you expect for each of the following...Ch. 8 - What shape do you expect for each of the following...Ch. 8 - What shape do you expect for each of the following...Ch. 8 - Prob. 8.45SPCh. 8 - Prob. 8.46SPCh. 8 - What shape do you expect for each of the following...Ch. 8 - What bond angles do you expect for each of the...Ch. 8 - What bond angles do you expect for each of the...Ch. 8 - Acrylonitrile is used as the starting material for...Ch. 8 - Predict values for all bond angles in dimethyl...Ch. 8 - Oceanographers study the mixing of water masses by...Ch. 8 - A potential replacement for the chlorofluorocarbon...Ch. 8 - Explain why cyclohexane, a substance that contains...Ch. 8 - Like cyclohexane (Problem 8.54), benzene also...Ch. 8 - Use VSEPR theory to answer the following...Ch. 8 - Draw an electron-dot structure for each of the...Ch. 8 - What is the difference in spatial distribution...Ch. 8 - The average CC bond dissociation energy (D) is 350...Ch. 8 - What hybridization do you expect for atoms that...Ch. 8 - What spatial arrangement of charge clouds...Ch. 8 - What hybridization would you expect for the...Ch. 8 - What hybridization would you expect for the...Ch. 8 - Oxaloacetic acid is an intermediate involved in...Ch. 8 - The atoms in the amino acid glycine are connected...Ch. 8 - Describe the hybridization of the carbon atom in...Ch. 8 - Describe the hybridization of each carbon atom in...Ch. 8 - Bupropion, marketed as Wellbutr in, is a heavily...Ch. 8 - Efavirenz, marketed as Sustiva, is a medication...Ch. 8 - What is the hybridization of the B and N atoms in...Ch. 8 - Prob. 8.71SPCh. 8 - Aspirin has the following connections among atoms....Ch. 8 - The cation [HCNXeF]+ is entirely linear. Draw an...Ch. 8 - Acrylonitrile (C3H3N) is a molecule that is...Ch. 8 - The odor of cinnamon oil is due to cinnamaldehyde,...Ch. 8 - The following molecular model is a representation...Ch. 8 - Prob. 8.77SPCh. 8 - Which of the following substances would you expect...Ch. 8 - Which of the following substances would you expect...Ch. 8 - Why is the dipole moment of SO2 1.63 D hut that of...Ch. 8 - Prob. 8.81SPCh. 8 - The class of ions PtX42 , where X is a halogen,...Ch. 8 - Prob. 8.83SPCh. 8 - Prob. 8.84SPCh. 8 - Prob. 8.85SPCh. 8 - Prob. 8.86SPCh. 8 - Prob. 8.87SPCh. 8 - What are the most important kinds of...Ch. 8 - Of the substances Xe, CH3Cl , and HF which has:...Ch. 8 - Methanol (CH3OH;bp=65C) boils nearly 230 °C higher...Ch. 8 - Prob. 8.91SPCh. 8 - Prob. 8.92SPCh. 8 - Prob. 8.93SPCh. 8 - A liquid sample contains methylamine (CH3NH2)...Ch. 8 - Prob. 8.95SPCh. 8 - What is the difference in spatial distribution...Ch. 8 - Prob. 8.97SPCh. 8 - Use the MO energy diagram in Figure 8.22b to...Ch. 8 - Use the MO energy diagram in Figure 8.22 a to...Ch. 8 - The C2 molecule can be represented by an MO...Ch. 8 - Prob. 8.101SPCh. 8 - Prob. 8.102SPCh. 8 - Prob. 8.103SPCh. 8 - Draw a molecular orbital energy diagram for Li2 ....Ch. 8 - Calcium carbide, CaC2 , reacts with water to...Ch. 8 - At high temperatures, sulfur vapor is...Ch. 8 - Carbon monoxide is produced by incomplete...Ch. 8 - Make a sketch showing the location and geometry of...Ch. 8 - Make a sketch showing the location and geometry of...Ch. 8 - Prob. 8.110MPCh. 8 - Prob. 8.111MPCh. 8 - Prob. 8.112MPCh. 8 - Prob. 8.113MPCh. 8 - Just as individual bonds in a molecule are often...Ch. 8 - Cyclooctatetraenedian ion, C8H82 , is an organic...
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