Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 16.5, Problem 7P
Interpretation Introduction
Interpretation:
The enediol rearrangement of the carbonyl carbon of fructose from
Concept Introduction:
In the enediol rearrangement of a monosaccharide, the base removes the proton from the carbon resulting in the formation of enolate ion. After the deprotonation, enediol is formed resulting in the formation of aldohexose and ketohexose by the base-catalyzed conversion.
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Students have asked these similar questions
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°)
JDownl
Q7: Identify the functional groups in these molecules
a)
CH 3
b) Aspirin:
HO
'N'
Capsaicin
HO
O
CH3
CH 3
Chapter 16 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Q2: Name the following alkanesarrow_forward1. Complete the following table in your laboratory notebook. Substance Formula Methanol CH3OH Ethanol C2H5OH 1-Propanol C3H7OH 1-Butanol C4H9OH Pentane C5H12 Hexane C6H14 Water H₂O Acetone C3H60 Structural Formula Molecular Weight (g/mol) Hydrogen Bond (Yes or No)arrow_forwardQ1: 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_forward
- Q3: 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_forwardThe ability of atoms to associate with each other depends ona) the electronic structure and its spatial orientation.b) the electron affinity.c) The other two answers are correct.arrow_forward
- What is the final volume after you reach the final temperature? I put 1.73 but the answer is wrong not sure why The initial volume of gas is 1.60 LL , the initial temperature of the gas is 23.0 °C°C , and the system is in equilibrium with an external pressure of 1.2 bar (given by the sum of a 1 bar atmospheric pressure and a 0.2 bar pressure due to a brick that rests on top of the piston). Then, as you did in Exercise 1, you heat the gas slowly until the temperature reaches 48.2 °Carrow_forwardQ4: Identify the type of Carbon ( methyl, primary, secondary, etc. ) indicated by this arrow.arrow_forwardQ3: Curved Arrows, Lewis Acids & Bases, Nucleophiles and Electrophiles Considering the following reactions: a) Predict the products to complete the reactions. b) Use curved electron-pushing arrows to show the mechanism for the reaction in the forward direction. Redraw some of the compounds to explicitly illustrate all bonds that are broken and all bonds that are formed. c) Label Lewis acids and bases, nucleophiles and electrophiles in the reactions. A. S + AICI 3 B. + H₂Oarrow_forward
- 3. A thermometer is placed in a test tube of chipped ice at -5.0 °C. The temperature is recorded at the time intervals shown below until room temperature is reached. Plot the data given below on graph paper and explain all flat, horizontal portions of the curve. Plot time on the X-axis! Time (min) Temperature (°C) 0 -5.0 2 -2.5 4 -1.0 6 0.0 10 0.0 15 0.0 20 0.0 25 0.0 30 1.5 35 4.0 40 8.0 45 11.5 50 15.0 55 17.5 60 19.0 65 20.0 70 20.0 75 20.0 80 20.0arrow_forwardNaming the Alkanes a) Write the IUPAC nomenclature of the compound below b) Draw 4-isopropyl-2,4,5-trimethylheptane, identify the primary, secondary, tertiary, and quaternary carbons. c) Rank pentane, neopentane and isopentane for boiling point. pentane: H3C-CH2-CH2-CH2-CH3 neopentane: CH3 H3C-Ċ-CH3 I CH3 isopentane: CH3 H3C-CH2-CH-CH3arrow_forwardWhich will evaporate faster, 1-Butanol or Pentane? Explain your choice.arrow_forward
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