ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Textbook Question
Chapter 2.1, Problem 3P
Use the electronegativity values shown in Figure 2-2 to rank the following bonds from least polar to most polar: H3C-Li, H3C-K, H3C-F, H3C-MgBr, H3C-OH
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Directions: Complete the data table below. It is not necessary to construct any models.
Number of bonds &
number of lone pairs
around central atom
Chemical
Valence
electrons
name
Formula
Lewis structure
NCI,
N-5
3 bonds
Nitrogen
CI- 7(3)
20 lone pairs
trichloride
Si-4
S-6(2)
Sis,
Silicon
disulfide
Н-1
C- 4
HCN
N-5
C-4
CF,CI,
F-7(2)
CI-7(2)
Ge-4
Germane
GeH,
H-1(4)
C-4
CSF,
S-6
F-7(2)
Selenium
Se-6
dichloride
SeCl,
CI-7(2)
AsF,
As-5
F-7(3)
arsenic
trifluoride
C-4(2)
Br-7(2)
Dibromoacetylene
chlorine gas
Cl:
CI-7(2)
dihydrogen
monoxide
DHMO
CH,O
C-4
H-1(2)
O-6
carbon
CF,
C-4
tetrafluoride
F-7(4)
For each full Lewis structure in question 4, draw a bond-line structure.
H H
a)
H-C-N-H
b)
H-N-C-N-H
H.
H H
O-C-C-N-H
c)
d) H-C-C-C-H
H-C-H
HICIH
HINIH
HICICIH
Draw the resonance structure indicated by the curved arrows. Assign formal charges.
H
H/:O:
H
H-C-C-C-Ċ—H
H H
H
Draw the molecule by placing atoms on the canvas and connecting them with bonds. Include all hydrogen atoms and nonbonding electrons. Show the formal charges of
all atoms in the correct structure.
Chapter 2 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
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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- Based on the atom connectivity shown bellow,evaluate the four resonance structure for the thiosulfate ion S2O3 ^2-. Use curved arrows to indicate how you get from one resonance structure to another. Assign formal changes to all atoms and determine which of these resonance structure is the most stable based on a formal charge analysis Explain your answer thoroughly. Look at the picture.arrow_forward1) Classify each bond below as ionic, non-polar covalent, or polar covalent. For the polar covalent compounds, indicate the direction of the dipole. Na-Br H-CI H3C-CH,CH, H,CO-H Br-Br H-OH H,C-CF, H-CH, F-CI H,C-OH Br-Mg -Br Li-CH,CH3 2) Determine the formal charge on each of the bold atoms below. Lone pairs have been drawn in for you. Hc- ー4 H,C-cEc: Hy .C H,C CH, Hc-C OH2 H. 3) Determine the formal charge on each of the bold atoms below. You must draw in lone pairs as appropriate. H C=CH HC CH N. H. HC PH H,C CH H,C H CH, H.arrow_forward4. The following are valid Lewis structures for CH3SOCH3. Label the formal charges and circle the best Lewis structure. H :ö: H H :0 H a) H-C=S-C-H b) Н—С—S— С-н H. H. H. H. Н :0: Н H :ö: H d) H-C=$-C-H c) Н—С—$—С-н H. H. H Harrow_forward
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