Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Question
Chapter 3.2, Problem 8P
Interpretation Introduction
Interpretation: The primary, secondary or tertiary amides in dolastatin are to be classified.
Concept introduction: Amides are the acid derivatives in which a nitrogen atom is bonded to an adjacent carbonyl carbon. They are synthesized by the reaction of an acid chloride with an amine. Amides are produced when esters react with
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Because amines are basic, they can often accept a proton. Draw the protonated structure of n-propylamine.
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Explain why
CH3 CH2 CH2NH2
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base.
Its water
solutions
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All
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nitrogen
atoms are
Brønsted
bases.
This
amine is a
proton
donor.
This
amine can
ассеpt a
proton
from a
proton
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Chapter 3 Solutions
Organic Chemistry (6th Edition)
Ch. 3.1 - Prob. 1PCh. 3.2 - (a) Classify the carbon atoms in each compound as...Ch. 3.2 - Problem 3.3 Classify a carbon atom by the number...Ch. 3.2 - Classify each alkyl halide and alcohol as , or...Ch. 3.2 - Prob. 5PCh. 3.2 - Prob. 6PCh. 3.2 - Draw the structure of a compound of molecular...Ch. 3.2 - Prob. 8PCh. 3.2 - Prob. 9PCh. 3.2 - Draw the structure of a compound fitting each...
Ch. 3.4 - Predict which compound in each pair has the higher...Ch. 3.4 - Prob. 17PCh. 3.4 - a Label the hydrophobic and hydrophilic portions...Ch. 3.5 - Prob. 21PCh. 3 - 3.29
Identify the functional groups in the...Ch. 3 - Prob. 32PCh. 3 - 3.31 For each alkane: (a) classify each carbon...Ch. 3 - 3.32 Identify the functional groups in each...Ch. 3 - 3.33 Identify each functional group located in the...Ch. 3 - 3.34 (a)Identify the functional groups in...Ch. 3 - Draw seven constitutional isomers with molecular...Ch. 3 - Prob. 38PCh. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Intramolecular force of attraction are often...Ch. 3 - 3.40 (a) Draw four compounds with molecular...Ch. 3 - 3.41 Rank the compounds in each group in order of...Ch. 3 - Explain why CH3CH2NHCH3 has higher boiling point...Ch. 3 - Prob. 45PCh. 3 - 3.44 Rank the following compounds in order of...Ch. 3 - Prob. 47PCh. 3 - 3.50 Predict the solubility of each of the...Ch. 3 - Prob. 52PCh. 3 - Prob. 53PCh. 3 - 3.53 THC is the active component in marijuana, and...Ch. 3 - Prob. 55PCh. 3 - Prob. 56PCh. 3 - 3.60 Quinapril (trade name Accupril) is a drug...Ch. 3 - 3.61 Answer each question about oxycodone, a...Ch. 3 - Prob. 65PCh. 3 - Prob. 66PCh. 3 - 3.64 Explain why A is less water soluble than B,...Ch. 3 - 3.65 Recall from section 1.10B that there is...
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Similar questions
- Draw the structure of the following three isomeric amides with chemical formula C6H11NO. Amide #1: (E)-N,N-dimethyl-2-butenamide Amide #2: (Z)-N-methyl-3-pentenamide Amide #3: (Z)-3-hexenamidearrow_forwardClassify the amides in dolastatin, an anticancer compound isolated from the Indian seahare Dolabella auricularia, as 1°, 2°, or 3°.arrow_forwardWhich 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_forward
- Draw a structural formula for each amine. (a) 2-Butanamine (b) 1-Octanamine (c) 2,2-Dimethyl-1-propanamine (d) 1,5-Pentanediamine (e) 2-Bromoaniline (f) Tributylaminearrow_forwardExplain 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 the structure of a compound of molecular formula C 9H 11NO that contains a benzene ring and a: (a) 1 ° amide; (b) 2 ° amide; (c) 3 ° amide.arrow_forward
- Classify the specified amides as 1º, 2º, or 3º. Part 1 Select the single best answer. Part 2 Oxytocin, sold under the trade name Pitocin, is a naturally occurring hormone used to stimulate uterine contractions and induce labor. Classify the specified amides in oxytocin as 1º, 2º, or 3º.arrow_forwardGiven that C6H11COOH has a pKa = 4.8 and C6H11N+H3 has a pKa = 10.7, (a) What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer? (b) What pH would you make the water layer to cause the carboxylic acid to dissolve in the ether layer and the amine to dissolve in the water layer?arrow_forwardN-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanone has a boiling point of 141 °C. These two isomershave a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boilingpoint difference than the two amine isomersarrow_forward
- Amides undergo hydrolysis under acidic conditions to give Select one: O Carboxylate ion and ammonium ion Carboxylic acid and amine Carboxylate ion and amine Carboxylic acid and ammonium ionarrow_forward8 (Chemical Connections 19C) Once it has been opened, and particularly if it has been left open to the air, a bottle of aspirin may develop a vinegar-like odor. Explain how this might happen.arrow_forward
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