EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Textbook Question
Chapter 29.7, Problem 11P
Locate the isoprene units in each compound.
a.
c. 
b. 
d. 
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n Feb 3
A
T
+
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
+
+
Chapter 29 Solutions
EBK ORGANIC CHEMISTRY
Ch. 29.2 - Problem 31.1
One component of jojoba oil is a wax...Ch. 29.3 - Problem 31.2
How would you expect the melting...Ch. 29.3 - Problem 31.3
Draw the products formed when...Ch. 29.3 - Problem 31.4
The main fatty acid component of the...Ch. 29.3 - Prob. 5PCh. 29.7 - Problem 31.10
Locate the isoprene units in each...Ch. 29.7 - Problem 31.11
Locate the isoprene units in...Ch. 29.7 - Problem 31.12
Write a stepwise mechanism for the...Ch. 29.7 - Prob. 14PCh. 29.8 - Prob. 15P
Ch. 29.8 - Prob. 16PCh. 29.8 - Prob. 17PCh. 29 - 31.17 Locate the isoprene units in each...Ch. 29 - Prob. 25PCh. 29 - Locate the isoprene units in each compound. a. e....Ch. 29 - 31.27 Classify each terpene and terpenoid in...Ch. 29 - Prob. 33PCh. 29 - Draw three-dimensional structures f or each...Ch. 29 - Prob. 37PCh. 29 - Prob. 38PCh. 29 - Prob. 39PCh. 29 - Prob. 40PCh. 29 - 31.38 Draw the products formed when cholesterol is...Ch. 29 - 31.39 Draw a stepwise mechanism for the following...Ch. 29 - 31.40 Draw a stepwise mechanism for the following...Ch. 29 - Prob. 44P
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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.arrow_forwardPart 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_forward
- Part 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_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_forward
- Part 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_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_forward
- The 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_forward7. Assign all of the protons on the spectrum below. A B 2 C E 2 1 3 6 4 3 2 1 0arrow_forward
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