Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 1, Problem 78P
There are three isomers with molecular formula C2H2Cl2. Draw their structures. Which one does not have a dipole moment?
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There are three constitutional isomers for the compound with the molecular formula C2H2Cl2.Draw your structures. Which of them does not have a dipole moment?
These two different C2H6O compounds are called structural (or constitutional) isomers -
compounds with the same molecular formula but with different connections among their
constituent atoms. If you must break and make new bonds in order to convert one structure into
the other (not simply rotate the model around), then they are structural isomers. The concept of
isomers is very important in organic chemistry and biochemistry.
This is also another instance where condensed formulas can be very useful because they can
help you distinguish two isomers apart even when you don't have models.
Exercise 8) Can your models be interconverted by rotating bonds, or must the bonds be
broken first? What does that mean about these two structures?
If you rotate the hydrogen atoms to a different position in a a model of C2H6 by turning about the central C—C bond, do you get different structural (or constitutional) isomers of C2H5Cl?
Chapter 1 Solutions
Organic Chemistry (8th Edition)
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.1 - a. How many protons do the following species...Ch. 1.1 - Chlorine has two isotopes, 35Cl and 37Cl; 75.77%...Ch. 1.2 - Prob. 4PCh. 1.2 - a. Write the ground-state electronic configuration...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? a. b. c. d.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 - Explain why HCL has a smaller dipole moment than...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. 16PCh. 1.4 - a. Draw two Lewis structure for C2H6O. b. Draw...Ch. 1.4 - Draw the lone-pair electrons that are not shown in...Ch. 1.4 - Prob. 20PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 22PCh. 1.4 - Prob. 23PCh. 1.5 - Draw the following orbitals: a. 3s orbital b. 4s...Ch. 1.6 - Prob. 25PCh. 1.6 - Indicate the kind of molecular orbital (, , , or )...Ch. 1.7 - What orbitals are used to form the 10 sigma bonds...Ch. 1.7 - Explain why a bond formed by overlap of s orbital...Ch. 1.9 - Put n number in each of the blanks: a. __ s...Ch. 1.9 - For each of the given species: a. Draw its Lewis...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. 35PCh. 1.13 - a. What are the relative lengths and strengths of...Ch. 1.13 - Prob. 38PCh. 1.14 - Describe the orbitals used in bonding and the bond...Ch. 1.15 - Which of the bond in a carbon-oxygen double bond...Ch. 1.15 - Would you expect a CC bond formed by sp2sp2...Ch. 1.15 - Caffeine is a natural insecticide found in the...Ch. 1.15 - a. What is the hybridization of each of the carbon...Ch. 1.15 - Predict the approximate bond angles for a. the CNC...Ch. 1.16 - What of the following molecules would you expect...Ch. 1.16 - Account for the difference in the shape and color...Ch. 1.16 - If the dipole moment of CH3F is 1.847 D and the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 50PCh. 1 - What is the hybridization of all the atoms (other...Ch. 1 - Draw the condensed structure of a compound that...Ch. 1 - Predict the approximate bond angles: a. the CNH...Ch. 1 - Prob. 54PCh. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - What is the hybridization of each of the carbon...Ch. 1 - Rank the bonds from most polar. a. CO, CF, CN b....Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 59PCh. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Predict the approximate bond angles for the...Ch. 1 - Prob. 62PCh. 1 - Draw the missing lone-pair electrons and assigns...Ch. 1 - a. Which of the indicated bonds in each molecule...Ch. 1 - For each of the following molecules, indicate the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 67PCh. 1 - Rank the following compounds from highest dipole...Ch. 1 - In which orbitals are the lone pairs in nicotine?Ch. 1 - Prob. 70PCh. 1 - Prob. 71PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 73PCh. 1 - Which compound has a larger dipole moment: CH3Cl...Ch. 1 - Prob. 75PCh. 1 - Explain why CH3Cl has a greater dipole moment than...Ch. 1 - a. Draw a Lewis structure for each of the...Ch. 1 - There are three isomers with molecular formula...
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- How many different structural isomers are there for octahedral molecules with the general formula AX2Y3 if A is the inner atom and there are no X-Y, X-X and Y-Y bonds?arrow_forwardOne way of naming alcohols is to name the alkyl group that is attached to the −OH and add the word alcohol. Write bond-line formulas for (a.) propyl alcohol and (b.) isopropyl alcohol.arrow_forwardDraw all the isomers of C4H10O using bond-line formulas.arrow_forward
- The carbon–carbon bond length in C2H2 is 1.20 Å, that in C2H4 is 1.34 Å, and that in C2H6 is 1.53 Å. Near which of these values would you predict the bond length of C2 to lie? Is the experimentally observed value, 1.31 Å, consistent with your prediction?arrow_forwardThere are three constitutional isomers with molecular formula C2H2Cl2. Draw their structures. Which one does not have a dipole moment?arrow_forwardLinoleic 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_forward
- 2. In measurements of the structure of molecules, some interesting trends are observed. The bond angle (H-C-H) in CH4 is 109°, as we would expect for a molecule in the tetrahedral VSEPR class. However, other molecules in the same VSEPR class, such as ammonia (NH3, H-N-H= 107°) and water (H2O, H-O-H = 105°), have smaller bond angles than expected. Explain the basis for the bond angle trend: CH4 > NH3 > H2O. %3Darrow_forwardUsing correct arrow formalism, write the contributors to the resonance hybrid structure of the acetate ion, CH3CO2, and Indicate any formal charges.arrow_forwardfive examples of structures with this formula (C6H12). At least one should containa ring, and at least one should contain a double bondarrow_forward
- Linoleic acid (below) 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. R, CH2 `H H' (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? R3. .CH2 R4 `H H `H H'arrow_forward1. For each of the following compounds and ions, draw the complete Lewis structure. All formal charges should be on the atoms that possess that formal charge. CH4 H3CBr CH3CH₂OH H₂S H₂SO4 (sulfuric acid) H³0+ CH3* 2. Convert the following condensed formulas into bond-line structures, making sure to draw in zig-zag formation. CH3CH₂CH₂CH₂CH₂CH₂CH₂CH3 FCH₂CH₂I H₂C=CHCH₂OH (CH3)2CHCOOHarrow_forwardCH3OCH3 and CH3C(O)CH3 have similar formulas and molar masses, but their dipole moments are quite different. Predict which compound has the higher boiling point and explain why.arrow_forward
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