Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
3rd Edition
ISBN: 9780137533268
Author: Paula Bruice
Publisher: PEARSON+
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Textbook Question
Chapter 13.1, Problem 1P
Identify the most acidic hydrogen in each compound.
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Q6: Using acetic acid as the acid, write the balanced chemical equation for the protonation of
the two bases shown (on the -NH2). Include curved arrows to show the mechanism.
O₂N-
O₂N.
-NH2
-NH2
a) Which of the two Bronsted bases above is the stronger base? Why?
b) Identify the conjugate acids and conjugate bases for the reactants.
c) Identify the Lewis acids and bases in the reactions.
Q5: For the two reactions below:
a) Use curved electron-pushing arrows to show the mechanism for the reaction in the
forward direction. Redraw the compounds to explicitly illustrate all bonds that are broken
and all bonds that are formed.
b) Label Bronsted acids and bases in the left side of the reactions.
c) For reaction A, which anionic species is the weakest base? Which neutral compound is
the stronger acid? Is the forward or reverse reaction favored?
d) Label Lewis acids and bases, nucleophiles and electrophiles in the left side of the
reactions.
A.
용
CH3OH
я хон
CH3O
OH
B. HBr
CH3ONa
NaBr
CH3OH
potential energy
Br
b) Translate the Newman projection below to its wedge-and-dash drawing.
F
H.
OH
CH3
CI
c) Isopentane (2-methylbutane) is a compound containing a branched carbon chain. Draw
a Newman projection of six conformations about the C2-C3 bond of isopentane. On the
curve of potential energy versus angle of internal rotation for isopentane, label each
energy maximum and minimum with one of the conformations.
0°
。
F
A
B
D
C
angle of internal rotation
E
F
360° (=0°)
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Chapter 13 Solutions
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2PCh. 13.1 - Prob. 3PCh. 13.1 - Prob. 4PCh. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6PCh. 13.2 - Prob. 7PCh. 13.3 - Prob. 8PCh. 13.3 - Prob. 9PCh. 13.3 - Prob. 10P
Ch. 13.4 - Prob. 11PCh. 13.5 - Prob. 12PCh. 13.5 - Prob. 13PCh. 13.6 - Prob. 14PCh. 13.7 - Prob. 16PCh. 13.8 - Prob. 17PCh. 13.8 - Prob. 18PCh. 13.8 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.10 - Propose a mechanism for the formation of...Ch. 13.10 - Prob. 22PCh. 13.10 - a. If the biosynthesis of palmitic acid were...Ch. 13 - Draw the enol tautomers for each of the following...Ch. 13 - Number the following compounds in order from...Ch. 13 - Prob. 26PCh. 13 - Explain why the pKa of a hydrogen bonded to the...Ch. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Using cyclopentanone as the reactant, show the...Ch. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - Describe how the following compounds can be...Ch. 13 - Prob. 46PCh. 13 - Which would require a higher temperature:...Ch. 13 - Prob. 48PCh. 13 - Propose a mechanism for the following reaction:Ch. 13 - Show how the following compounds could be...Ch. 13 - Prob. 51PCh. 13 - Prob. 52P
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- Q1: Compare the relative acidity in each pair of compounds. Briefly explain. (a) CH3OH vs NH 3 (b) HF vs CH3COOH (c) NH3 vs CH4 (d) HCI vs HI (e) CH3COOH vs CH3SH (f) H₂C=CH2 vs CH3 CH3 (g) compare the acidity of the two bolded hydrogens O. H N- (h) compare the acidity of the two bolded hydrogens, draw resonance structures to explain H H Harrow_forwardQ3: Rank the following molecules in order of decreasing boiling point: (a) 3-methylheptane; (b) octane; (c) 2,4-dimethylhexane; (d) 2,2,4-trimethylpentane.arrow_forwardQ5: Conformations of Alkanes a) Draw a Newman Projection of the compound below about the C2-C3 bond. H3C Cli... H IIIH Br CH3arrow_forward
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