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Provide a structural formula for each of the following compounds: (a) 2 -Ethyl-1-butanamine (f) \(N\) -Allylcyclohexylamine (b) \(N\) -Ethyl-l-butanamine (g) \(N\) -Allylpiperidine (c) Dibenzylamine (h) Benzyl 2-aminopropanoate (d) Tribenzylamine (i) 4 - \((N, N\) -Dimethylamino)cyclohexanone (e) Tetraethylammonium hydroxide (j) 2,2 -Dimethyl-1,3-propanediamine

Short Answer

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Refer to the solution steps for detailed structural formulas of each compound.

Step by step solution

01

Drawing 2-Ethyl-1-butanamine

1. Begin with the butane chain: draw a four-carbon linear chain. 2. At position 2, add an ethyl group (-CH鈧侰H鈧). 3. Attach an amine group (-NH鈧) at position 1. 4. The structural formula is: CH鈧-CH(CH鈧侰H鈧)-CH鈧-CH鈧-NH鈧.
02

Drawing N-Ethyl-1-butanamine

1. Start with the butane chain: draw a four-carbon chain. 2. Attach an ethyl group (CH鈧僀H鈧-) to the nitrogen atom instead of a hydrogen. 3. The structural formula is: CH鈧-CH鈧-CH鈧-CH鈧-NHCH鈧侰H鈧.
03

Drawing Dibenzylamine

1. Draw a nitrogen atom linked to two benzyl groups (each benzyl group is a phenyl group, -C鈧咹鈧, attached to a -CH鈧- group). 2. The structural formula is: C鈧咹鈧匔H鈧-NH-CH鈧侰鈧咹鈧.
04

Drawing Tribenzylamine

1. Draw a nitrogen atom linked to three benzyl groups. 2. The structural formula is: (C鈧咹鈧匔H鈧)鈧僋.
05

Drawing Tetraethylammonium hydroxide

1. Draw a nitrogen atom surrounded by four ethyl groups, making it a quaternary ammonium salt. 2. Include the hydroxide ion (OH鈦). 3. The structural formula is: (CH鈧僀H鈧)鈧凬鈦 OH鈦.
06

Drawing N-Allylcyclohexylamine

1. Draw a cyclohexane ring. 2. Attach an amine group with an allyl group (CH鈧=CHCH鈧-) linked to the nitrogen. 3. The structural formula is: C鈧咹鈧佲倎-NH-CH鈧侰H=CH鈧.
07

Drawing N-Allylpiperidine

1. Draw a piperidine ring (a 6-membered ring with one nitrogen atom). 2. Attach an allyl group to the nitrogen atom. 3. The structural formula is: (CH鈧)鈧匩-CH鈧侰H=CH鈧.
08

Drawing Benzyl 2-aminopropanoate

1. Draw a propanoate chain: CH鈧-CH(NH鈧)-COO- 2. Attach a benzyl group (-C鈧咹鈧匔H鈧-) to the oxygen in the ester group. 3. The structural formula is: C鈧咹鈧匔H鈧侽OC-CH(NH鈧)-CH鈧.
09

Drawing 4-(N,N-Dimethylamino)cyclohexanone

1. Draw a cyclohexanone, which is a cyclohexane ring with a ketone group (C=O) on one carbon (one of the carbon atoms in the ring is bonded to an oxygen atom via a double bond). 2. At the 4-position, attach an N,N-dimethylamino group (-N(CH鈧)鈧). 3. The structural formula is: O=C(C鈧匟鈧佲個-N(CH鈧)鈧).
10

Drawing 2,2-Dimethyl-1,3-propanediamine

1. Draw a propane chain (CH鈧僀H鈧侰H鈧). 2. Add dimethyl groups at position 2, creating a (CH鈧)鈧-C- structure. 3. Attach amine groups at positions 1 and 3. 4. The structural formula is: CH鈧-CH(NH鈧)-C(CH鈧)鈧-CH鈧-NH鈧.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Amines
Amines are organic compounds that contain a nitrogen atom bonded to one or more alkyl groups. These alkyl groups can vary, leading to different types of amines, such as primary (one alkyl group), secondary (two alkyl groups), and tertiary (three alkyl groups) amines. In terms of structure:
  • Primary amines have the general formula \( ext{RNH}_2\), where R is an alkyl group.
  • Secondary amines are formulated as \( ext{R}_2 ext{NH}\).
  • Tertiary amines have the formula \( ext{R}_3 ext{N}\).
Amines are key building blocks in organic chemistry due to their role in creating complex molecules. Their reactivity and basicity make them important in many biological and industrial processes.
They can form hydrogen bonds, which significantly influence their boiling points and solubility.When naming amines, the suffix "-amine" is often used, and the carbon group attached to the nitrogen defines the prefix. For example, in the case of 2-Ethyl-1-butanamine, the compound consists of a butane chain with an ethyl group and an amine group bonded to it.
Benzyl groups
Benzyl refers to a specific substituent or group in organic chemistry that consists of a phenyl ring (C鈧咹鈧) attached to a CH鈧 group. Unlike the simple phenyl group, which is directly bonded, the benzyl group connects via an extra methylene (-CH鈧-) bridge.
  • The structure of benzyl can be represented as \( ext{C}_6 ext{H}_5 ext{CH}_2}\).
  • Benzyl groups are often aromatic due to the phenyl ring's stability.
This group is quite prevalent in many chemical transformations and synthesis reactions.
For example, in dibenzylamine, the nitrogen is bonded with two benzyl groups, highlighting its capability to connect aromatic rings to nitrogen atoms.
Benzyl groups frequently appear in discussions about protecting groups, due to their protective properties in various reactions.
Cyclohexane
Cyclohexane is a simple, saturated cyclic hydrocarbon with the formula \( ext{C}_6 ext{H}_{12} \). It forms a six-membered ring, which is entirely composed of carbon atoms, and each carbon atom is bonded to two hydrogen atoms. Cyclohexane is significant due to:
  • Its ability to exist in various conformations, such as the chair and boat forms.
  • The chair conformation being more stable, as it minimizes the steric strain between hydrogen atoms.
Cyclohexane is often used as a non-polar solvent in chemical reactions and as a standard for calibrating NMR spectroscopy.
In the context of N-Allylcyclohexylamine, a cyclohexane ring is the backbone structure where an allyl group is substituted onto an amine. This highlights cyclohexane's role as a flexible component, allowing various substitutions and modifications.
Piperidine
Piperidine is a saturated heterocyclic compound structured in a six-membered ring, similar to cyclohexane, but with one nitrogen atom replacing one of the carbon atoms. It has the formula \( ext{C}_5 ext{H}_{11} ext{N} \), and is known as a secondary amine, which comes from the nitrogen atom forming bonds with other groups.
  • Piperidine rings provide a crucial framework for synthesizing many pharmaceutical compounds due to their stability and reactivity.
  • They act as useful scaffolds in organic synthesis, given their ability to undergo various chemical modifications.
In N-Allylpiperidine, the nitrogen in the piperidine ring is bonded to an allyl group. This shows how piperidine can form complex compounds with robust biological activities.
Piperidine's structure and function make it a staple in medicinal chemistry, as it forms the basis for creating many medicinal molecules and natural products.

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Most popular questions from this chapter

Outline syntheses of each of the following from aniline and any necessary organic or inorganic reagents. (a) \(p\) -Nitroaniline (b) 2,4 -Dinitroaniline (c) \(p\) -Aminoacetanilide

Write the structure of the product formed on reaction of acetanilide with each of the following: (a) Lithium aluminum hydride, followed by water (b) Nitric acid and sulfuric acid (c) Sulfur trioxide and sulfuric acid (d) Bromine in acetic acid (e) tert-Butyl chloride, aluminum chloride (f) Acetyl chloride, aluminum chloride (g) \(6 \mathrm{M}\) hydrochloric acid, reflux (h) Aqueous sodium hydroxide, reflux

-Dimethylaniline and pyridine are similar in basicity, whereas \(4-(N, N\) -dimethylamino)pyridine is considerably more basic than either. Apply resonance principles to identify the more basic of the two nitrogens of 4- \((N, N\) -dimethylamino)pyridine, and suggest an explanation for its enhanced basicity.

Both alkyl- and arylamines have a low barrier for pyramidal inversion at nitrogen, which prevents the separation of chiral amines into their enantiomers. The barrier for inversion at nitrogen in alkylamines is approximately \(25 \mathrm{~kJ} / \mathrm{mol}(6 \mathrm{kcal} / \mathrm{mol})\), whereas for arylamines it is much lower, on the order of \(6.3 \mathrm{~kJ} / \mathrm{mol}(1.5 \mathrm{kcal} / \mathrm{mol})\). Can you suggest a reason for the difference?

Three of the following amines can be prepared by the Gabriel synthesis; three cannot. Write equations showing the successful applications of this method. (a) Butylamine (d) 2-Phenylethylamine (b) Isobutylamine (e) N-Methylbenzylamine (c) tert-Butylamine (f) Aniline

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