Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 1, Problem 1.36P
Using the values of electronegativity given in Table 1.5, predict which indicated bond in each set is more polar, and using the symbols δ+ and δ–, show the direction of its polarity.
- (a) CH3—OH or CH3O—H
- (b) CH3—NH2 or CH3— PH2
- (c) CH3— SH or CH3S—H
- (d) CH3—F or H—F
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The arrangement of atoms in several biologically important molecules is given here. Complete the Lewis
structures of these molecules by adding multiple bonds and lone pairs. Do not add any more atoms.
(a) the amino acid serine:
車
0-H
H-C-H
H
Н—N—с—с—о—н
H
(b)
нон
H-N-C-N-H
(c) pyruvic acid:
ноо
н—с—с—с—о—н
H.
(d) uracil:
H
(e) carbonic acid:
H-0-C-0-H
Calculate the Enthalpy Change (ΔH) from average bond energies, which have been listed below in KJ/mol, for the following reaction and identify the nature of the reaction:
CH3COOH + CH3OH → CH3COOCH3 + H2O
[C‒H: 413; C‒C: 347; C=O: 745; C=C: 614; Cl‒Cl: 239, C‒O: 358; O‒H: 467]
(a) Complete the Lewis structure for vinyl chloride by
showing all unshared pairs of electrons.
(b) Predict the H-C-H, H-C-C, and Cl-C-H
bond angles in this molecule.
(c) Does vinyl chloride have polar bonds? Is it a
polar molecule? Does it have a dipole?
Chapter 1 Solutions
Organic Chemistry
Ch. 1.1 - Prob. 1.1PCh. 1.2 - Prob. 1.2PCh. 1.2 - Judging from their relative positions in the...Ch. 1.2 - Classify each bond as nonpolar covalent or polar...Ch. 1.2 - Using the symbols and +, indicate the direction...Ch. 1.2 - Draw Lewis structures showing all valence...Ch. 1.2 - Draw Lewis structures for these ions and show...Ch. 1.3 - Draw Lewis structures and condensed structural...Ch. 1.3 - Prob. 1.9PCh. 1.3 - Prob. 1.10P
Ch. 1.3 - Prob. 1.11PCh. 1.3 - Prob. 1.12PCh. 1.4 - Predict all bond angles for these molecules. (a)...Ch. 1.5 - The geometry of carbon in diamond is tetrahedral,...Ch. 1.5 - Because of their spherical shape, C60 molecules...Ch. 1.5 - What best describes the CCC bond angles in C60? 1....Ch. 1.5 - Prob. 1.14PCh. 1.7 - Describe the bonding in these molecules in terms...Ch. 1.8 - Prob. 1.16PCh. 1.8 - Prob. 1.17PCh. 1.8 - Prob. 1.18PCh. 1.9 - Draw three contributing structures of the...Ch. 1.9 - What is the hybridization state of the circled...Ch. 1.9 - The molecule shown on the right in the example in...Ch. 1.9 - Prob. CQCh. 1.9 - The following structure is called imidazolium....Ch. 1 - Write the ground-state electron configuration for...Ch. 1 - Identify the atom that has each ground-state...Ch. 1 - Define valence shell and valence electron.Ch. 1 - How many electrons are in the valence shell of...Ch. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Write Lewis structures for these compounds. Show...Ch. 1 - Write Lewis structures for these ions. Show all...Ch. 1 - Prob. 1.29PCh. 1 - Some of these structural formulas are incorrect...Ch. 1 - Following the rule that each atom of carbon,...Ch. 1 - Following are several Lewis structures showing all...Ch. 1 - Which statements are true about electronegativity?...Ch. 1 - Why does fluorine, the element in the upper right...Ch. 1 - Arrange the single covalent bonds within each set...Ch. 1 - Using the values of electronegativity given in...Ch. 1 - Prob. 1.37PCh. 1 - Use VSEPR to predict bond angles about each...Ch. 1 - Use VSEPR to predict bond angles about each atom...Ch. 1 - Use VSEPR to predict the geometry of these ions....Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - Draw structural formulas for (a) The four primary...Ch. 1 - Draw structural formulas for the three tertiary...Ch. 1 - Prob. 1.47PCh. 1 - Identify the functional groups in each compound.Ch. 1 - Draw a three-dimensional representation for each...Ch. 1 - Tetrafluoroethylene, C2F4, is the starting...Ch. 1 - Which statements are true about resonance...Ch. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Are the structures in each set valid contributing...Ch. 1 - State the orbital hybridization of each...Ch. 1 - Describe each highlighted bond in terms of the...Ch. 1 - Following is a structural formula of the...Ch. 1 - Draw a Lewis structure for methyl isocyanate,...Ch. 1 - What is the hybridization of the highlighted atoms...Ch. 1 - Using cartoon representations, draw a molecular...Ch. 1 - In what kind of orbitals do the lone-pair...Ch. 1 - Draw the delocalized molecular orbitals for the...Ch. 1 - Prob. 1.64APCh. 1 - Each compound contains both ions and covalent...Ch. 1 - Predict whether the carbon-metal bond in these...Ch. 1 - Prob. 1.67APCh. 1 - Phosphorus is immediately under nitrogen in the...Ch. 1 - Draw a Lewis structure for the azide ion, N3. (The...Ch. 1 - Cyanic acid, HOCN, and isocyanic acid, HNCO,...Ch. 1 - In Chapter 6, we study a group of organic cations...Ch. 1 - Many reactions involve a change in hybridization...Ch. 1 - Following is a structural formula of benzene,...Ch. 1 - Following are three contributing structures for...Ch. 1 - (a) Draw a Lewis structure for the ozone molecule,...Ch. 1 - The following two compounds are isomers; that is,...Ch. 1 - In future chapters, we will encounter...Ch. 1 - Prob. 1.78AP
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- Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?arrow_forwardI need this solution, Calculate the Enthalpy Change (ΔH) from average bond energies, which have been listed below in KJ/mol, for the following reaction and identify the nature of the reaction: CH3COOH + CH3OH → CH3COOCH3 + H2O [C‒H: 413; C‒C: 347; C=O: 745; C=C: 614; Cl‒Cl: 239, C‒O: 358; O‒H: 467arrow_forwardUsing the symbols 8- and &+, indicate the direction of polarity, if any, in each covalent bond. (а) С—СІ (b) S-H (c) C-S (d) Р—Нarrow_forward
- See Figures 4.5a and 4.7. Can propane (C3H8) form isomers? Explain.arrow_forwardUse the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?arrow_forwardConvert each of the following molecular models into a skeletal structure, and give the formula of each. Only the connections between atoms are shown; multiple bonds are not indicated (gray = C, red = O, blue = N, ivory = H).arrow_forward
- The structural formula for ethane is (a) What is the molecular formula for ethane?(b) What is its empirical formula?(c) Can we infer from this drawing that the H—C—H bond angles are 90 degrees?arrow_forwardDraw Lewis structures for the following compounds. Remember to enclose ions in square brackets. On your answer sheet, state the number of valence electrons in each compound. (a) NaCN (b) CH 3 Br (c) Ca(OCl) 2arrow_forwarda) Draw the Lewis structure of H3PO4. b) In H3PO4, one P-O bond has a different bond length than the other three. Would it be shorter or longer than the others? Justify your answer.arrow_forward
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