ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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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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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.
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-hexenamide
Arrange the following amines in order of increasing basicity. For example, an answer of 1234 would indicate that you think 1 is least basic and 4 is most basic
Chapter 3 Solutions
ORGANIC CHEMISTRY
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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- 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 the reactions for the following products (any or all) (include all products).arrow_forwardLSD (a hallucinogen) and codeine (a narcotic) are structurally more complex derivatives of 2-phenylethanamine. Identify the atoms of 2-phenylethanamine in each of the following compounds.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_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_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_forwardClassify 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_forwardFill-in the missing reagents and products for the synthesis of amines.arrow_forward
- Draw the structure of M-P-V-G, and indicate its amide bonds.arrow_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_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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