Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Textbook Question
Chapter 4, Problem 10E
Propanal (bp 48°C) and propanol (bp 97°C), both found on Table 4.2, have very similar surfaceareas and dipole moments. Construct an explanation for the large difference in boiling pointsbetween the two.
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19. Based on molecular mass and dipole moment of the five
compounds in the table below, which one should have the
highest boiling point?
Dipole Moment
(D)
Substance
Molecular Mass
(amu)
Propane, CH3CH2CH3
Dimethyl ether, CH3OCH3
Methylchloride, CH3C1
Acetaldehyde, CH;CHO
Acetonitrile, CH3CN
44
0.1
46
1.3
50
1.9
44
2.7
41
3.9
B) CH;CN
E) CH3CH2CH3
C) CH3CHO
A) CH3OCH3
D) CH;CI
Chapter 2
[References]
H3C
HB
CH3
На,
CH3
CH3
D
H3C
B
НО
Cholestanol differs from cholesterol only in the absence of a double bond in ring B.
Draw the three-dimensional structure of cholestanol, and then determine the orientation of the following groups:
#1: H at the junction of rings C & D with respect to ring C|
#2: H at the junction of rings A & B with respect to ring B
#3: Methyl at the junction of rings C & D with respect to ring C|
O I
The “free-base” form of cocaine (C17H21NO4) and its protonatedhydrochloride form (C17H22ClNO4) are shownbelow; the free-base form can be converted to the hydrochlorideform with one equivalent of HCl. For clarity, notall the carbon and hydrogen atoms are shown; each vertexrepresents a carbon atom with the appropriate number ofhydrogen atoms so that each carbon makes four bonds toother atoms.(a) One of these forms of cocaine is relatively water-soluble:which form, the free base or the hydrochloride?(b) One of these forms of cocaine is relatively insoluble inwater: which form, the free base or the hydrochloride?
(c) The free-base form of cocaine has a solubility of 1.00 g in6.70 mL ethanol (CH3CH2OH). Calculate the molarityof a saturated solution of the free-base form of cocaine inethanol.(d) The hydrochloride form of cocaine has a solubility of1.00 g in 0.400 mL water. Calculate the molarity of a saturatedsolution of the hydrochloride form of cocaine inwater.(e) How many mL of a…
Chapter 4 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 4 - Prob. 1CTQCh. 4 - Figure 4.1 is a cartoon depiction of liquid water...Ch. 4 - Prob. 3CTQCh. 4 - Prob. 4CTQCh. 4 - In HF , neither H nor F holds a full formal charge...Ch. 4 - Prob. 6CTQCh. 4 - Prob. 7CTQCh. 4 - Prob. 8CTQCh. 4 - Within any one section of Table 4.2, boiling...Ch. 4 - Prob. 10CTQ
Ch. 4 - Prob. 11CTQCh. 4 - Prob. 12CTQCh. 4 - Prob. 13CTQCh. 4 - Prob. 14CTQCh. 4 - Prob. 15CTQCh. 4 - Prob. 16CTQCh. 4 - Prob. 17CTQCh. 4 - Prob. 18CTQCh. 4 - Prob. 19CTQCh. 4 - Prob. 20CTQCh. 4 - Prob. 21CTQCh. 4 - Prob. 22CTQCh. 4 - (E) Label each of the following as strong acid,...Ch. 4 - Prob. 24CTQCh. 4 - Draw the structure of the conjugate base of water....Ch. 4 - Does Cl have a conjugate acid? If so, what is it?...Ch. 4 - Draw the conjugate base of CH4 (methane).Ch. 4 - For the previous four questions, label each...Ch. 4 - Prob. 29CTQCh. 4 - According to the conventions above, what is the...Ch. 4 - Draw an arrow on Figure 4.13 representing Hrxn4 ....Ch. 4 - Prob. 32CTQCh. 4 - Add a + or above each curved arrow in Figure 4.11...Ch. 4 - Prob. 34CTQCh. 4 - Prob. 35CTQCh. 4 - Prob. 36CTQCh. 4 - Prob. 37CTQCh. 4 - Prob. 38CTQCh. 4 - Prob. 39CTQCh. 4 - Prob. 40CTQCh. 4 - Prob. 41CTQCh. 4 - Prob. 42CTQCh. 4 - Prob. 43CTQCh. 4 - Prob. 44CTQCh. 4 - Prob. 45CTQCh. 4 - Prob. 46CTQCh. 4 - For NH3 (ammonia) and H2O (water)... a. Use curved...Ch. 4 - Prob. 48CTQCh. 4 - Prob. 49CTQCh. 4 - Prob. 50CTQCh. 4 - Prob. 51CTQCh. 4 - Prob. 52CTQCh. 4 - Prob. 53CTQCh. 4 - Prob. 1ECh. 4 - Prob. 2ECh. 4 - Prob. 3ECh. 4 - Prob. 4ECh. 4 - Prob. 5ECh. 4 - Prob. 6ECh. 4 - Prob. 7ECh. 4 - Prob. 8ECh. 4 - Propanal (bp 48°C) and propanol (bp 97°C), both...Ch. 4 - Rank the following molecules from lowest to...Ch. 4 - Prob. 12ECh. 4 - For each molecule below, draw the conjugate acid...Ch. 4 - For each structure you drew in the answer to the...Ch. 4 - Mark each of the following statements True or...Ch. 4 - Organic chemistry is a bit like cooking. Later in...Ch. 4 - Prob. 17ECh. 4 - Prob. 18ECh. 4 - Are endothermic reactions favorable or...Ch. 4 - Prob. 20ECh. 4 - Is bond formation endothermic or exothermic? Write...Ch. 4 - Summarize the relationship between pKa and acid...Ch. 4 - Summarize the relationship between pKa and base...Ch. 4 - Prob. 25ECh. 4 - Consider the following bases: a. For each base...Ch. 4 - Prob. 27ECh. 4 - The following are equivalent ways of asking about...Ch. 4 - Prob. 29E
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- a) Which of the following compounds is (are) capable of H-bonding to itself? Circle all that apply. 여 он Но но A в D E b) Which of the compounds above cannot be a H-bond donor but can be a H-bond acceptor? c) Which of the compounds above would you expect to have the highest boiling point? Provide a brief explanation. ZIarrow_forwardNitromethane is an organic compound with the molecular Draw a complete Lewis structure for the conjugate acid of nitromethane that shows all bonds, unshared electron pairs, and minimized formal charges, where appropriate. formula CH, NO,. Draw a complete Lewis structure that shows all bonds, unshared electron pairs, and minimized formal charges, where appropriate. H H 1. H : 0 :arrow_forward(a) Which of the AF3 molecules in Fig. 1 will have a nonzero dipole moment? Explain. b) Which of the AF4 molecules in Fig. 2 will have a zero dipole moment? Explain.arrow_forward
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