Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 2.SE, Problem 29AP
Use the electronegativity table given in Figure 2-2 to predict which bond in each of the following pairs is more polar, and indicate the direction of bond polarity for each compound.
(a) H3C-Cl or Cl-Cl
(b) H3C-H or H-Cl
(c) HO-CH3 or (CH3)3Si-CH3
(d) H3C-Li or Li-OH
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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
Draw a Lewis structure for each of the following molecules:
(a) chlorodifluoromethane, CHClF2
(b) propanoic acid, C2 H5CO2H (basic structure pictured below)
(c) acetonitrile, CH3CH (the framework is H3C-C-N)
(d) allene, H3CCCH2
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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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
- Chemistry (a) Write three more resonance structures for each of compounds 1 and 2. (b) In each of compounds 1 and 2, determine which resonance structure contributes the most and explain your answer. (c) Are the 3/4 structures resonance structures or different compounds? Same question for 5/6 structures. Explain your answers.arrow_forwardStructural Formulaarrow_forwardDraw the molecules in Problem 1.61 using line structuresarrow_forward
- Using just a periodic table (not a table of electronegativities), decide which of these is likely to be the most polar bond. Explain your answer! (a) C-F (b) S-F (c) Si-F (d) O-Farrow_forwardDraw a Lewis Structure for each of the following species and assign formal charge where appropriate. Using electronegative values from the period table that was provided identify polar covalent bonds and label the atoms δ+ and δ−. For each of the molecules indicate whether or not it has a dipole moment. (a)CH5N (b) HCN (c) H2CO (d) CH3NC(e) CH3SOCH3 (f) H6BNarrow_forward2. Identify the bond (ionic, polar covalent, or covalent) existing in the following compounds: (a) HCI (b) KF (c) the CC in H,CCH, (d) H,S (e) the NN in H,NNH,. Ise the symhols 6 and6 to show the direction of the polarity of the indicated bond in H,C-OH.arrow_forward
- Name the following compounds:arrow_forward(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?arrow_forward16. Which of the following structures is the CORRECT resonance structure of the following. molecule: (A) (B) (C) (D) CH3- CH₂ CH3 -H CH₂CH3 CH₂CH-CH₂ CH3 CH3arrow_forward
- 3. Using electronegativity difference, indicate the type of bond between the following atoms: (a) Li-Cl(b) C-Br(c) F-Cl(d) Br-Brarrow_forwardCalculate the electronegativity difference │EN│ for each of the following bonds (include one decimal place, e.g., "0.0") (a) H-Cl (b) Na-O (c) Si-P (d) I-Farrow_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_forward
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