Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 24.SE, Problem 51AP
Histamine, whose release in the body triggers nasal secretions and constricted airways, has three nitrogen atoms. List them in order of increasing basicity and explain your ordering.
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n Feb 3
A
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
+
+
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 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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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
- 8. 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_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_forward
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