PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 23, Problem 23.63P
Synthesize each compound from cyclohexanone and organic halides having
a.
b.
c.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Part VI.
Ca H 10 O is the molecular formula of compound Tom and gives the
in the table below. Give a possible structure for compound Tom.
13C
Signals summarized
C1
C2
C3
C4
C5
C6
C7
13C shift (ppm)
23.5
27.0
33.0
35.8
127
162
205
DEPT-90
+
DEPT-135
+
+
2. Using the following data to calculate the value of AvapH o of water at 298K. AvapH o of water at
373K is 40.7 kJ/mol; molar heat capacity of liquid water at constant pressure is 75.2J mol-1 K-1 and
molar heat capacity of water vapor at constant pressure is 33.6 J mol-1 K-1.
Part VII. Below are the 'HNMR
13
3 C-NMR, COSY 2D- NMR, and HSQC 20-NMR (Similar with HETCOR but axes are reversed) spectra of an
organic compound with molecular formula C6H13 O. Assign chemical shift values to the H and c atoms of the
compound. Find the structure. Show complete solutions.
Predicted 1H NMR Spectrum
ли
4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8
f1 (ppm)
Chapter 23 Solutions
PKG ORGANIC CHEMISTRY
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Prob. 23.2PCh. 23 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 23 - Prob. 23.4PCh. 23 - Problem 23.5 Which bonds in the following...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - Prob. 23.8PCh. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
Knowledge Booster
Learn more about
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
- 3. Draw the expanded structural formula, the condensed structural formula, and the skeletal structural formula for 2-pentene. expanded structure: Condensed structure: Skeletal formula: 4. Draw the expanded structural formula, the condensed structural formula, and the skeletal structural formula for 2-methyl-3-heptene. expanded structure: Condensed structure: Skeletal formula: following structurearrow_forwardPart IV. Propose a plausible Structure w/ the following descriptions: a) A 5-carbon hydrocarbon w/ a single peak in its proton decoupled the DEPT-135 Spectrum shows a negative peak C-NMR spectrum where b) what cyclohexane dione isomer gives the largest no. Of 13C NMR signals? c) C5H120 (5-carbon alcohol) w/ most deshielded carbon absent in any of its DEPT Spectivaarrow_forward13C NMR is good for: a) determining the molecular weight of the compound b) identifying certain functional groups. c) determining the carbon skeleton, for example methyl vs ethyl vs propyl groups d) determining how many different kinds of carbon are in the moleculearrow_forward
- 6 D 2. (1 pt) Limonene can be isolated by performing steam distillation of orange peel. Could you have performed this experiment using hexane instead of water? Explain. 3. (2 pts) Using GCMS results, analyze and discuss the purity of the Limonene obtained from the steam distillation of orange peel.arrow_forwardPart III. Arrange the following carbons (in blue) in order of increasing chemical shift. HO B NH 2 A CIarrow_forward6. Choose the compound that will produce the spectrum below and assign the signals as carbonyl, aryl, or alkyl. 100 ō (ppm) 50 0 7. 200 150 Assign all of the protons on the spectrum below. 8. A B 4 E C 3 ō (ppm) 2 1 0 Choose the compound that will produce the spectrum below and assign the signals to the corresponding protons. OH 6 OH 3 2 1 0 4 ō (ppm)arrow_forward
- In the Thermo Fisher application note about wine analysis (Lesson 3), the following chromatogram was collected of nine components of wine. If peak 3 has a retention time of 3.15 minutes and a peak width of 0.070 minutes, and peak 4 has a retention time of 3.24 minutes and a peak width of 0.075 minutes, what is the resolution factor between the two peaks? [Hint: it will help to review Lesson 2 for this question.] MAU 300 200 T 34 5 100- 1 2 CO 6 7 8 9 0 2.4 2.6 2.8 3.0 3.2 3.4 3.6 3.8 4.0 4.2 4.4 4.6 4.8 5.0 5.2 Minutes 3.22 0.62 1.04 O 1.24arrow_forwardThe diagram shows two metals, A and B, which melt at 1000°C and 1400°C. State the weight percentage of the primary constituent (grains of C) that would be obtained by solidifying a 20% alloy of B. 1000°C a+L L+C 900°С 12 α a+C 45 1200 C L+y 140096 C+Y a+ß 800°C 700°C C+B 96 92 a+B 0 10 20 30 40 50 60 70 80 90 100 A % peso B Barrow_forward8. Choose the compound that will produce the spectrum below and assign the signals to the corresponding protons. 2 4 3 ō (ppm) OH 4 6 6 СОН 2 1 0arrow_forward
- 7. Assign all of the protons on the spectrum below. A B 2 C E 2 1 3 6 4 3 2 1 0arrow_forwarde. If (3R,4R)-3,4-dichloro-2,5-dimethylhexane and (3R,4S)-3,4-dichloro-2,5-dimethylhexane are in a solution at the same concentration, would this solution be expected to rotate plane polarized light (that is, be optically active)? Please provide your reasoning for your answer. [If you read this problem carefully, you will not need to draw out the structures to arrive at your answer...]arrow_forward1. How many neighbors does the proton that produces the multiplet below have? 2. 3. اللـ Draw a partial structure from the multiplet below. (The integration of the multiplet is 6) M Using the additivity constants found in appendix G of your lab manual, calculate the approximate chemical shifts of the protons indicated below. (Show your work!!!) B A Br SHarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY