Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 59AP
We’ll see in the next chapter that organic molecules can be classified according to the
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For each compound in the table below, decide whether there would be any hydrogen-bonding force between molecules of the compound, or between molecules
of the compound and molecules of water.
name
acetic acid
dimethyl ether
compound
hypobromous acid
formula or Lewis
structure
H :0:
H-C-C-O-H
H
H
H-C-0-C H
H
H
T
HBrO
|
H
Between
molecules of the
compound?
yes
O O
no
O yes
no
yes
hydrogen-bonding force
no
Between molecules of
the compound and
molecules of water?
O O
yes
no
yes
no
yes
no
X
Rank the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest boiling
point, choose 2 next to the substance with the next highest boiling point, and so on.
substance
A
B
C
chemical symbol,
chemical formula
or Lewis structure
:0:
||
H-C-H
Co
H₂
H-C-H
||
H-C-H
boiling point
(Choose one)
(Choose one)
(Choose one) ✓
(Choose one)
X
Ś
V
0
E
Designate the structural features of polar molecules using partial charges or arrows.
Ethyl heptanoate is responsible for grape aroma. It has the chemical formula C9H1802 but structural
formula CH3-(CH2)s-COO-CH2-CH3. A structure is shown below. Which bonds would feature partial
charges? Designate them using partial charges or arrows.
H
H
H
| H
H
H
H
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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- Formamide, HC(O)NH2, is prepared at high pressures from carbon monoxide and ammonia, and serves as an industrial solvent (the parentheses around the O indicate that it is bonded only to the carbon atom and that the carbon atom is also bonded to the H and the N atoms). Two resonance forms (one with formal charges) can be written for formamide. Write both resonance structures, and predict the bond angles about the carbon and nitrogen atoms for each resonance form. Are they the same? Describe how the experimental determination of the HNH bond angle could be used to indicate which resonance form is more important.arrow_forwardSuccessive substitution of F atoms for H atoms in the molecule NH3 produces the molecules NH2F, NHF2, and NF3. a. Draw Lewis structures for each of the four molecules. b. Using VSEPR theory, predict the geometry of each of the four molecules. c. Specify the polarity (polar or nonpolar) for each of the four molecules.arrow_forwardFor each compound in the table below, decide whether there would be any hydrogen-bonding force between molecules of the compound, or between molecules of the compound and molecules of water. name formic acid compound dibromomethane acetic acid formula or Lewis structure :0: || H-C-O-H CH₂Br₂ H :0: | || H-C-C-O-H H Between molecules of the compound? 00 00 yes no yes no yes hydrogen-bonding force no Between molecules of the compound and molecules of water? 00 00 yes no yes no yes no Xarrow_forward
- || Predicting deviations from ideal bond angles Consider the carbonyl fluoride (CF₂O) molecule. What is the central atom? Enter its chemical symbol. How many lone pairs are around the central atom? What is the ideal angle between the carbon-fluorine bonds? Compared to the ideal angle, you would expect the actual angle between the carbon-fluorine bonds to be ... 口。 (choose one) (choose one) about the same bigger smallerarrow_forward✔nk the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest Bolling puint, choose 2 next to the substance with the next highest boiling point, and so on. substance A B C D chemical symbol, chemical formula or Lewis structure H H-C-F: H :O: | || HIC-C-F: 1 H H H H :O: | || HIC-C-0-H F₂ boiling point ✓ (Choose one) 1 (highest) 2 34 4 (lowest) (Choose one) ✓ (Choose one) ✓ (Choose one) ✓arrow_forwardRank the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest boiling point, choose 2 next to the substance with the next highest boiling point, and so on. substance A B C D chemical symbol, chemical formula or Lewis structure H :O: H | || | H-C-C-C-H H | | H Ar | | H H Ag H H | | H-C-C-C-O-H 1 H | H boiling point (Choose one) (Choose one) (Choose one) X (Choose one 1 (highest) 2 3 4 (lowest) 5arrow_forward
- compound hydrogen-bonding force Between Between molecules of formula or Lewis molecules of the the compound and molecules of water? name structure compound? H H | Н — С | | yes yes N-chloromethylamine - no no H. yes yes hydrogen iodide HI no no :0: || н —с —с-о — н H yes yes acetic acid no no H O Oarrow_forwardName 5 common organic compounds that are found in your home. Draw their Lewis structures and give their molecular formula. Encircle and identify the functional group/s that is/ are present in each molecule. Write your answers in another sheet of paper. Ex. Acetic acid in vinegar Substance Molecular formula Lewis structure CH,COOH - more preferable H-C+C 0-H Acetic acid C2H4O2 in vinegar H Carboxylic acid エーO-エarrow_forwardDirections: Arrange the following substances according to increasing polarity by getting the difference in the electronegativities of the atoms in the compound. You may use your periodic table as a reference for the electronegativity of the elements. In the case of compounds with multipie elements, get the difference in electronegativity of the encircled elements. Least polar substance Most polar substance H-C=N H-H Н-F Na - Cl H-О-Нarrow_forward
- Consider the molecule of furan. Its Lewis structure is shown. H X Is furan polar? If yes, consider which side of the molecule has partial negative charge and which - partial positive. Then, indicate the direction of the dipole moment relative to the molecule as shown. Non-polar, zero dipole moment. Polar, the dipole vector points along one of the C-O bonds. Polar, the dipole vector points along one of the C-H bonds. Polar, the dipole vector points along the vertical axis. Polar, the dipole vector points along the horizontal axis.arrow_forwardRank the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest boiling point, choose 2 next to the substance with the next highest boiling point, and so on. substance A B с D : 0: chemical symbol, chemical formula or Lewis structure H-O- - H 1 C H CO - 0 | C | H H Al₂O3 0₂ — :O: -0 - - H boiling point ✓ (Choose one) 1 (highest) 2 3 4 (lowest) (Choose one) (Choose one) (Choose one)arrow_forwardRank the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest boiling point, choose 2 next to the substance with the next highest boiling point, and so on. substance A B C D H chemical symbol, chemical formula or Lewis structure H | HC H | N H- HIC - C C - H Η H HIC C I | H H — — - H Cr O-H Ar :O: O HIC - H C H - H - X boiling point (Choose one) ◊ (Choose one) (Choose one) (Choose one) ✪ Sarrow_forward
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