Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 3, Problem 3.7P
Explain why the boiling point of propanamide,
considerably higher than the boiling point of
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Explain why
CH3 CH2 CH2NH2
is a Brønsted
base.
Its water
solutions
are basic.
All
substances
containing
nitrogen
atoms are
Brønsted
bases.
This
amine is a
proton
donor.
This
amine can
ассеpt a
proton
from a
proton
donor.
Because amines are basic, they can often accept a proton. Draw the protonated structure of n-propylamine.
The following amines have the same molecular formula (C5H13N), but their boiling points are significantly different.
Explain why.
H
`NH2
2-Methylbutan-1-amine
Boiling point = 97 °C
N-Methylbutan-2-amine
Boiling point = 84 °C
N-Ethyl-N-methylethan-1-amine
Boiling point = 65 °C
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 3.1PCh. 3 - Prob. 3.2PCh. 3 - Draw the structure of a compound fitting each...Ch. 3 - Draw structures that fit each description and name...Ch. 3 - What types of intermolecular forces are present in...Ch. 3 - Prob. 3.6PCh. 3 - Explain why the boiling point of propanamide, is...Ch. 3 - Predict which compound in each pair has the higher...Ch. 3 - Prob. 3.9PCh. 3 - Prob. 3.10P
Ch. 3 - a Label the hydrophobic and hydrophilic portions...Ch. 3 - Prob. 3.12PCh. 3 - Prob. 3.13PCh. 3 - Prob. 3.14PCh. 3 - Prob. 3.15PCh. 3 - Nonactin and valinomycin each contain only two...Ch. 3 - Prob. 3.17PCh. 3 - Problem 3.26 Label the electrophilic and...Ch. 3 - Problem 3.27 Considering only electron density,...Ch. 3 - The fact that sweet-tasting carbohydrates like...Ch. 3 - 3.29
Identify the functional groups in the...Ch. 3 - Prob. 3.22PCh. 3 - 3.32 Identify the functional groups in each...Ch. 3 - Draw the seven constitutional isomers having...Ch. 3 - 3.33 Identify each functional group located in the...Ch. 3 - Draw seven constitutional isomers with molecular...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Intramolecular force of attraction are often...Ch. 3 - 3.40 (a) Draw four compounds with molecular...Ch. 3 - Prob. 3.32PCh. 3 - Explain why CH3CH2NHCH3 has higher boiling point...Ch. 3 - Prob. 3.34PCh. 3 - Prob. 3.35PCh. 3 - Explain the observed trend in the melting points...Ch. 3 - Prob. 3.37PCh. 3 - Prob. 3.38PCh. 3 - Prob. 3.39PCh. 3 - 3.48 Explain why diethylether and have similar...Ch. 3 - Prob. 3.41PCh. 3 - 3.50 Predict the solubility of each of the...Ch. 3 - Prob. 3.43PCh. 3 - Prob. 3.44PCh. 3 - THC is the active component in marijuana, and...Ch. 3 - Prob. 3.46PCh. 3 - Prob. 3.47PCh. 3 - Prob. 3.48PCh. 3 - Label the electrophilic and nucleophilic sites in...Ch. 3 - By using only electron density arguments,...Ch. 3 - Prob. 3.51PCh. 3 - Prob. 3.52PCh. 3 - Prob. 3.53PCh. 3 - Prob. 3.54PCh. 3 - Prob. 3.55PCh. 3 - Recall from section 1.10B that there is restricted...
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- The product of this reaction is: O CI secondary amide secondary amine primary amide tertiary amide primary amine + 2NH3arrow_forward454 | Chapter 15 Amines (a) Which of the two nitrogen atoms in epibatadine is 54 the stronger base? (b) Mark the three stereocenters in this molecule. Cl H N Narrow_forward2. Below is the structure of caffeine. Circle and label (a) an amide functional group, (b) a tertiary amine, and (c) the purine ring system. O CH3 N CH-N O N CH3 N H 3. Caffeine is an alkaloid and has base characteristics. Of the four nitrogens in the structure of the molecule, which one(s) would give it this property? sneltro bem 4. Besides caffeine, what else is extracted into the tea? Why can you use the basic salt, Na₂CO3, sodium carbonate, to remove this material? 5. What criterion is used for the purity of a sample of caffeine?arrow_forward
- Explain why the boiling point of propanamide, CH3CH2CONH2, is considerably higher than the boiling point of N,Ndimethylformamide, HCON(CH3)2 (213 °C vs. 153 °C), even though both compounds are isomeric amides.arrow_forwardDraw condensed formulas for the carboxylic acid and amine that form the following amides:arrow_forwardThe five parts of question 16 relate to the following three molecules: N-H А в с A (a) Which of the three molecules above are structural isomers? (b) Which of the molecules contains a carbon with linear geometry? (c) Which molecule contains a tertiary amine? (d) Which molecule only contains sp³ hybridized atoms (not including hydrogen)? (e) Which molecule is chiral? Circle the stereocentre in this molecule.arrow_forward
- Which of the following is a tertiary amine? C) N-H CH₂ N-CH₂ H₂C b) NH₂ CH₂ CH₂ H₂CH N CH, d) H₂c-c CH, C-CH₂ CHarrow_forwardWhich of the following compounds is a 3º amide? Ph 1 3 2 N(CH₂CH3)2 2 in de la adm Ph NH-Bu Ph NH-iPr Ph NH₂ 3arrow_forwardUsing the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- The structure of Synthroid, used to treat hypothyroidism (low-functioning thyroid), is shown below. Highlight the phenol, the ether, the amine, and the carboxylic acid. Is the carboxylic acid in its neutral or ionic form? Is the amine in its neutral or ionic form? он OH Synthroidarrow_forward< app.101edu.co Classify and describe the properties of the following nitrogen containing compound. O CI O + Question 13.a of 25 CH3 N Classify the following amine. H CH3 A) primary amine B) secondary amine C) tertiary amine @=J D) tertiary amine salt E) quaternary ammonium saltarrow_forwardIndicate the category of base to which the following compound belongs: Сасоз Hydride Amine O Carbonate O Bicarbonate Hydroxide Alkoxide O Carbanion O Amidearrow_forward
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