OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.SE, Problem 30AP
Tell whether the following pairs of compounds are identical, constitutional isomers, stereoisomers, or unrelated.
(a) cis-1, 3-Dibromocyclohexane and trans-1, 4-dibromocyclohexane
(b) 2, 3-Dimethylhexane and 2, 3, 3-trimethy1pentane
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T
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4. (2 pts) Draw the structure of the major component of the Limonene isolated. Explain how
you confirmed the structure.
5. (2 pts) Draw the fragment corresponding to the base peak in the Mass spectrum of
Limonene.
6. (1 pts) Predict the 1H NMR spectral data of R-Limonene.
Proton NMR: 5.3 pon multiplet (H Ring
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
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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.
Chapter 4 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- 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)arrow_forward3. 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_forward
- 13C 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_forward6 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_forward
- 6. 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_forwardIn 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_forward
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