Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.28P
Which species are Lewis acids?
a.
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Students have asked these similar questions
Here are the energies (in kcal/mol) for staggered and eclipsed interactions
for CH, CC, and CBr bonds
eclipsed (0°) staggered (60°)
bonds
CH/CH
1.0
0.0
CH/CC
1.3
0.0
Br:
CC/CC
3.0
0.9
Br
CH/CBr
1.8
0.0
CC / CBr
3.3
1.0
CBr / CBr
3.7
1.2
a) I've drawn the Newman projection for one of the staggered conformations of the molecule
above, looking down the C2-C3 bond. Draw Newman projections for the other two staggered
and the three eclipsed conformations (in order).
CH₂
H3C.
H'
H
Br
b) Calculate the relative energies for each of the conformations and write them below each
conformation.
90. Draw the stereoisomers obtained from each of the following reactions:
a.
H₂
b.
H₂
C.
H₂
Pd/C
Pd/C
Pd/C
36. The emission spectrum below for a one-electron (hydrogen-like) species in the gas
phase shows all the lines, before they merge together, resulting from transitions to the
first excited state from higher energy states. Line A has a wavelength of 434 nm.
BA
Increasing wavelength, λ
(a) What are the upper and lower principal quantum numbers corresponding to the lines
labeled A and B? (b) Identify the one-electron species that exhibits the spectrum.
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- f) The unusual molecule [2.2.2] propellane is pictured. 1) Given the bond length and bond angles in the image, what hybridization scheme best describes the carbons marked by the askerisks? 2) What types of orbitals are used in the bond between the two carbons marked by the askerisks? 3) How does this bond compare to an ordinary carbon-carbon bond (which is usually 1.54 Å long)? H₂C H₂C CH2 1.60Å ハ C. * CH₂ H₂C * C H₂ 120°arrow_forwardQuestion Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributorarrow_forwardCan you show me or determine the longest carbon chain, which is octane? Potentially highlight it in different sections to show me, plz, or individually?arrow_forward
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- a. The structure of the bicarbonate (hydrogen carbonate) ion, HCO3-, HCO3 " is best described as a hybrid of several contributing resonance forms, two of which are shown here. HO :0: HO + :Ö: Bicarbonate is crucial for the control of body pH (for example, blood pH 7.4). A more self-indulgent use is in baking soda, where it serves as a source of CO2 CO2 gas, which gives bread and pastry their fluffy constituency. (i) Draw at least one additional resonance form. = (ii) Using curved "electron-pushing" arrows, show how these Lewis structures may be interconverted by movement of electron pairs. (iii) Determine which form or forms will be the major contributor(s) to the real structure of bicarbonate, explaining your answer on the basis of the criteria in Section 1-5.arrow_forwardCalibri 11 + BIL NAME: Jaylena M A student is investigating the ctect of volume on pressure during a lab activity. The student uses the following volumes (mL). 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 28, 30, 33, 34, 35, 38, 40, 42, 44. 46, and 50. As the volume changed they measured the following pressures (atm) 11.0, 10.5, 10.0, 9.2. 8.5, 78, 75, 7.0, 6.8, 6.5, 6.0, 5.9, 5.5, 5.0, 4.8, 4.5, 4.2, 3.9, 3.8, 3.5, 3.3, 3.2, 3.0, 2.9. What is the independent variable? Volume Imla What is the dependent variable? Pressure Jatm Use the data and make a PROPER data table. Volume 1mL) Pressure latm 110arrow_forwardDraw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor.arrow_forward
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