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.

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.

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter16: Amines And Amides

Section: Chapter Questions

Problem 16.61E

See similar textbooks

Related questions

Q: Explain why the boiling point of propanamide, CH3CH2CONH2, is considerably higher than the boiling…

A: Physical properties like boiling point depend upon the molecular mass and intermolecular hydrogen…

Q: Classify each amine in the following compounds as 1°, 2°, or 3°. NH2 a. H,N b. CH,CH20. N-CH,…

A: NH3 is ammonia R-NH2 is primary amine i.e. N attached to one alkyl and two hydrogen atoms forms a…

Q: Assign IUPAC names to the following amides: || CH;CH,CH-C-NH, a. CH,CH; b. CH;CH,CH,-C-NH-…

Q: Draw the structure of the following three isomeric amides with chemical formula C,HNO. Amide #1:…

Q: Reactions carried out: a) aniline with tosyl chlorode b) N-methylaniline with tosyl choride c)…

A: a.Aniline reacts with tosyl chloride to give product by simple elimination of HCl. The skeletal…

Q: What are the reactions between propanamide and NaOH, H2O; then H3O+?

Q: Determine the hybridization around the N atom in each amine, andexplain why cyclohexanamine is 106…

A: Hybridization is a hypothetical concept which involves mixing of two or more pure orbitals. When…

Q: Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed…

Q: Arrange the amines in order of increasing boiling point (lowest first). methylamine I ethylamine II…

Q: Disubstituted amides often have lower boiling points than unsubstituted amides. What is the main…

A: In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with…

Q: Explain the effect of acid on the solubility of the water-insoluble amines.

A: Amines are compound that contains functional group nitrogen with its lone pair, it's formula may…

Q: Classify the amides in dolastatin, an anticancer compound isolated from the Indian seahare Dolabella…

A: The given molecule is represented as follows:

Q: КОН CH,OCH,CH,CON(CH, ,

A: Acid base reactions are faster. Here, a base can abstract the most acidic hydrogen.

Q: Write equations for the hydrolysis of these amides in concentrated aqueous HCl. Show all products as…

A: Cyclic amide is named as lactam. Lactams are named according to the ring size number. An example…

Q: Draw the structure of the following three isomeric amides with chemical formula CgH1¡NO. Amide #1:…

A: Isomers are defined as compounds having the same molecular formula but have a difference in the…

Q: Account for the fact that most low-molecular-weight amines are very soluble in water, whereas low-…

A: Solubility: The solubility of a chemical substance in water depends on the polar nature of the…

Q: 2. Which of the following is a tertiary amine. Encircle the substituents that make it tertiary. CH3…

Q: accept

A: n-propylamine is basic because the nitrogen of the amine group consists of a lone pair which is…

Q: Features of the structure of imino acids. Formation of amides from amino acids.

A: Amino acids

Q: Predict the major products formed when the following amines undergo exhaustivemethylation, treatment…

Q: Write equations for the hydrolysis of these amides in concentrated aqueous HCl. Show all products as…

A: The given amide is,

Q: Consult E Table 5.1 and classify each nitrogen-containing functional group in the anesthetic…

Q: Classify the amides in dolastatin, an anticancer compound isolated from the Indian seahare Dolabella…

A: When we talk about the primary, secondary and tertiary the N that is attached to 1 carbon atom is…

Q: Which Amine is the weakest base? Explain why. A.) NH3 B.) NH2CH3 C.) NH2F D.) NHCH2CH3 E.)…

A: Alkyl group and halogen group(an electron releasing (+I) and group) increases electron density at N…

Q: neutral because of the polarity are unique as they do not behave like any of the other amines…

A: Basicity is tendency to available lone pair of electrons for an acid.

Q: What amine is formed by reduction of each amide?

A: (a) 1° amine is formed by the reduction of the given compound.

Q: Account for the experimental behavior of each class of amines (primary, secondary and tertiary)…

A: A question based on organic chemistry, which is to be accomplished.

Q: What is true regarding protein backbones? The protein backbone is different for each protein and…

A: Proteins are the chain of amino acid that assembe through peptide bonds.Proteins are generally high…

Q: Arrange the amines in order of increasing boiling point (lowest first). methylamine I ethylamine II…

A: Greater is the intermolecular force, higher will be the boiling point. Greater is the molecular…

Q: 1 * The pentacyclic amide is called the B ring Beta-lactam 0 Kama-lactam 0 Delta lactams 0 Omega…

A: Given, Pentacycilc amide

Q: You are trying to identify an unknown amine from a list of potential candidates. You have the…

A: Ammonia is a basic compound and reacts with acid. In the presence of acid like HCl it will react and…

Q: Classify each of the following salts as an amine salt or a quaternary ammonium salt. CH3-NH-CH, Br…

Q: What amides will form attached amine on treatment with LiAlH4 ?

A: During the reduction reaction of amide to amine by LiAlH4, the carbonyl group (C=O) is reduced to…

Q: 1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes…

A: The nitrogen atom of DABCO attacks the carbonyl carbon of ester group which makes the alkoxy group a…

Q: Characterize the amides I and Il in caffeine. caffeine O lis a primary amide, Il is a tertiary amide…

Q: A tertiary amine is more basic compared to a secondary amine. (A) True B False

A: Amines are Lewis base due to the presence of a lone pair of electrons on the nitrogen atom of amine.

Q: The C-N distance in an amide bond is approximately 1.32 Å. A typical C-N single bond is 1.45 Å,…

A: The C–N distance in an amide bond is approximately 1.32 Å. A typical C–N single bond is 1.45Å, while…

Q: Which amines cannot be prepared by reduction of an amide?

A: Reduction of amides can be done using LiAlH4 to prepare primary (RNH2), secondary (R2NH) and…

Q: Arrange the following amines in order of increasing boiling point, lowest bp to highest bp:…

A: Given: Primary amine: (CH3)2CHCH2CH2NH2 Secondary amine: (CH3)2CHCH2NHCH3 Tertiary amines:…

Q: Draw the structure of the following three isomeric amides with chemical formula C6H11NO. Amide #1:…

Q: Why are the boiling points of tertiary amines lower than those of corresponding primary and…

A: Amines are organic compounds that contain nitrogen atoms with a lone pair. Basically, they are…

Q: Draw the structure of the amine salt produced when each of the following amines reacts with HCI. a.…

A: Since you have posted a question with multiple sub-parts, we will solve the first three subparts for…

Q: Classify the amides in dolastatin, an anticancer compound isolated from the Indian seahare Dolabella…

A: The given molecule is represented as follows:

Q: Which amines cannot be prepared by reduction of an amide?

A: The amines which cannot be prepared by reduction of an amide has to be given,

Q: Why is the amine N atom more nucleophilic than the amide N atom in CH3CONHCH2CH2CH2NHCH3?

A: Nucleophilicity of a chemical species depends on availability of electrons on it. Factors such as…

Q: Draw structures for the following amines. - 3-decanamine - N,N-dipropylbutanamine…

A: The IUPAC is a system that contains some rule that helps in the naming of the organic compounds. The…

Q: Predict the major products formed when the following amines undergo exhaustivemethylation, treatment…

A: Elimination reactions: Organic reactions contain the removal of a group of atoms from a molecule by…

Question

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Three amide isomers, N,N-dimethylformamide, N-methylacetamide, and propanamide, have respective boiling points of 153 °C (426 K), 202 °C (475 K), and 213 °C (486 K). Explain these boiling points in light of their structural formulas.
N-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 isomers
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
Complete this table for different amine compounds. Chemical propylamine quaternary ammonium ion methylphenylamine Molecular formula C3H9N C₂H7N C5H13N C4H10N Structural formula (CH3)3N (CH3)2NH CH 3 I (CH₂) 11 | H3C(CH2) 11 -N-(CH₂)11CH3 NHCH3 (CH₂)11 CH3 CH3CH2CH2-NH-CH3 + Classification Tertiary Quaternary Tertiary Secondary
Draw and name compounds that meet these descriptions:(a) Three different amides with the formula C6H13NO(b) Three different esters with the formula C5H10O2
The C-N distance in an amide bond is approximately 1.32 Å. A typical C-N single bond is 1.45Å, while a typical C=N double bond is 1.25 Å. Explain this observation and describe how thebonding in amides restricts the conformations amides can adopt.
Draw all the possible amide isomers with C3H7NO molecular formula.
Draw the amide formed when 1-methylethylamine (CH3CH(CH3)NH2) is heated with each carboxylic acid.
Tertiary amides have how many C-N bonds?
Write the common name for each amine. HỌC—N—CH,CH3 H₂C-CH₂-CH₂-CH₂ Ethylbutylamine common name: Incorrect HC—CH,—N—CH,—CHy CH₂ CH3 diethylethylamine common name: Incorrect These compounds are tertiary amines.
Below is the structure of Clemastine and its functional groups. Which of the following statements regarding Clemastine and its functional groups is NOT true? * Ether Tertiary amines CH CH3 Halogenated aromatic hydrocarbon Aromatic hydrocarbon Aliphatic hydrocarbons Clemastine (Tavist) Aromatic hydrocarbon is lipophilic Halogenated aromatic hydrocarbon is lipophilic. Tertiary amine is hydrophobic. Ether is hydrophilic.
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 CH