Concept explainers
a) cis-1,2-Cyclohexanedicarboxylic acid
Interpretation:
The structure of cis-1,2-cyclohexanedicarboxylic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain
To give:
The structure of cis-1,2-cyclohexanedicarboxylic acid.
Answer to Problem 32AP
The structure of cis-1,2-cyclohexanedicarboxylic acid is
Explanation of Solution
The name shows that the compound has a cyclohexane ring with two carboxylic acid groups in 1,2 positions arranged in the same side of the ring.
The structure of cis-1,2-cyclohexanedicarboxylic acid is
b) Heptanedioic acid
Interpretation:
The structure of heptanedioic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.
To give:
The structure of heptanedioic acid.
Answer to Problem 32AP
The structure of heptanedioic acid is
Explanation of Solution
The name shows that the compound has a seven carbon straight chain with two carboxyl groups at theb ends.
The structure of heptanedioic acid is
c) 2-Hexen-4-ynoic acid
Interpretation:
The structure of 2-hexen-4-ynoic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.
To give:
The structure of 2-hexen-4-ynoic acid.
Answer to Problem 32AP
The structure of 2-hexen-4-ynoic acid is
Explanation of Solution
The name shows that the compound has a six carbon straight chain with a carboxylic group, a double bond between C2 & C3 and a triple bond between C4 & C5.
The structure of 2-hexen-4-ynoic acid is
d) 4-Ethyl-2-propyloctanoic acid
Interpretation:
The structure of 4-ethyl-2-propyloctanoic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.
To give:
The structure of 4-ethyl-2-propyloctanoic acid.
Answer to Problem 32AP
The structure of 4-ethyl-2-propyloctanoic acid is
Explanation of Solution
The name shows that the compound is an octane derivative and has a carboxyl group, a propyl group on C2 and an ethyl group on C4.
The structure of 4-ethyl-2-propyloctanoic acid is
e) 3-Chlorophthalic acid
Interpretation:
The structure of 3-chlorophthalic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.
To give:
The structure of 3-chlorophthalic acid.
Answer to Problem 32AP
The structure of 3-chlorophthalic acid is
Explanation of Solution
The name indicates that the compound is a benzene derivative with two carboxyl groups on C1 & C2 and a chlorine atom on C3.
The structure of 3-chlorophthalic acid is
f) Triphenylacetic acid
Interpretation:
The structure of triphenylacetic acid is to be given.
Concept introduction:
The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.
To give:
The structure of triphenylacetic acid.
Answer to Problem 32AP
The structure of triphenylacetic acid is
Explanation of Solution
The structure of acetic acid is CH3COOH. The name of the compound given indicates that it has three phenyl groups instead of the three hydrogen atoms present in methyl group in acetic acid.
The structure of triphenylacetic acid is
g) 2-Cyclobutenecarbonitrile
Interpretation:
The structure of 2-cyclobutenecarbonitrile is to be given.
Concept introduction:
Simple open chain nitriles are named by adding –nitrile as suffix to the alkane name, with the nitrile carbon numbered as C1. Nitriles can also be names as derivatives of carboxylic acids by replacing the –ic acid or –oic acid ending with –onitrile. The nitrile carbon is not numbered but the carbon to which it is attached is numbered ac C1. If another carboxylic acid derivative is present in the same molecule, the prefix –cyano is used for the –CN group.
To give:
The structure of 2-cyclobutenecarbonitrile.
Answer to Problem 32AP
The structure of 2-cyclobutenecarbonitrile is
Explanation of Solution
The name shows that the compound has a nitrile group attached to a cyclobutene ring with a double bond between C2 & C3.
The structure of 2-cyclobutenecarbonitrile is
h) m-Benzoylbenzonitrile
Interpretation:
The structure of m-benzoylbenzonitrile is to be given.
Concept introduction:
Simple open chain nitriles are named by adding –nitrile as suffix to the alkane name, with the nitrile carbon numbered as C1. Nitriles can also be names as derivatives of carboxylic acids by replacing the –ic acid or –oic acid ending with –onitrile. The nitrile carbon is not numbered but the carbon to which it is attached is numbered ac C1. If another carboxylic acid derivative is present in the same molecule, the prefix –cyano is used for the –CN group.
To give:
The structure of m-benzoylbenzonitrile.
Answer to Problem 32AP
The structure of m-benzoylbenzonitrile is
Explanation of Solution
The name shows that the compound has a benzene ring attached to a nitrile group and a benzoyl group with meta relationship.
The structure of m-benzoylbenzonitrile is
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
- Nonearrow_forwardn 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 Ringarrow_forwardPart 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 + +arrow_forward
- 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
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning