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Chapter 6: Problem 23

Draw structures for the following compounds: (a) tert-butyl alcohol (b) 2,3 -dimethoxybutane (c) cis-2,3-epoxyhexane (d) THF (e) ethylene oxide

Short Answer

Expert verified
Structures: tert-butyl alcohol, 2,3-dimethoxybutane, cis-2,3-epoxyhexane, THF, ethylene oxide.

Step by step solution

01

Title - Draw tert-butyl alcohol

tert-Butyl alcohol has a central carbon atom bonded to three methyl groups and one hydroxyl group. To draw it, place the hydroxyl (OH) group on the central carbon (C) and attach three methyl groups (CH3) to it in a tetrahedral arrangement.
02

Title - Draw 2,3-dimethoxybutane

2,3-Dimethoxybutane has a butane skeleton with methoxy groups (-OCH3) attached to the 2nd and 3rd carbons. Draw a four-carbon chain and attach a methoxy group to both the second and third carbon atoms.
03

Title - Draw cis-2,3-epoxyhexane

cis-2,3-Epoxyhexane has a hexane backbone with an epoxide (three-membered ether ring) positioned at the 2nd and 3rd carbons in the cis configuration. Draw a six-carbon chain, position the epoxide ring between the 2nd and 3rd carbon atoms in a cis arrangement, ensuring the same side substitution for adjacent hydrogens.
04

Title - Draw THF

THF (tetrahydrofuran) is a five-membered ring with four carbon atoms and one oxygen atom. Draw a five-membered ring consisting of four carbons and an oxygen.
05

Title - Draw ethylene oxide

Ethylene oxide is a three-membered ring composed of two carbon atoms and one oxygen atom. Draw the three-membered ring with the oxygen atom.

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Key Concepts

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

tert-butyl alcohol structure
tert-Butyl alcohol, also known as t-butyl alcohol, is an example of a tertiary alcohol. The structure includes a central carbon atom bonded to three methyl groups (CH3) and one hydroxyl group (OH). To draw its structure, follow these simple steps:
  • Place a central carbon atom (C).
  • Attach a hydroxyl group (OH) to this central carbon.
  • Connect three methyl groups (CH3) to the same central carbon.
This structure forms a tetrahedral arrangement. The central carbon is bonded to four different groups, representing the multiple connections typical in organic chemistry.
2,3-dimethoxybutane structure
2,3-Dimethoxybutane is an ether with a butane backbone. It has methoxy groups (-OCH3) attached to the second and third carbons. Here’s how to draw it:
  • Draw a straight chain with four carbon atoms to represent the butane backbone.
  • Identify and label the second and third carbon atoms in this chain.
  • Attach a methoxy group (-OCH3) to both the second and third carbon atoms.
The key aspect of this structure is the positioning of the methoxy groups, both on adjacent carbons, which modifies the chemical properties of the butane chain.
cis-2,3-epoxyhexane structure
cis-2,3-Epoxyhexane is characterized by its six-carbon chain (hexane) and an epoxide ring (three-membered ether ring) between the second (2) and third (3) carbon atoms in a cis configuration. To draw its structure:
  • Draw a straight chain of six carbon atoms to represent hexane.
  • Identify and mark the second and third carbons in the chain.
  • Create an epoxide ring that connects these two carbon atoms.
Ensure that the hydrogen atoms attached to these carbon atoms are on the same side, representing the 'cis' configuration. This is important because the 'cis' positioning affects the compound’s stereochemistry and overall reactivity.
THF structure
THF (tetrahydrofuran) is a cyclic ether, and its structure consists of a five-membered ring containing four carbon atoms and one oxygen atom. Here’s how to draw it:
  • Sketch a five-sided ring where each corner represents a carbon or oxygen atom.
  • Substitute one of the carbon atoms with an oxygen atom.
The result should be a ring with one oxygen atom and four carbon atoms. This ring structure is stable and is commonly used as an industrial solvent due to its ability to dissolve both polar and non-polar compounds.
ethylene oxide structure
Ethylene oxide is distinguished by its three-membered ring structure consisting of two carbon atoms and one oxygen atom. Here are the steps to draw it:
  • Draw a triangle to represent the ring.
  • Label two of the vertices as carbon atoms (C).
  • Label the remaining vertex as an oxygen atom (O).
This three-membered ring is highly strained, making ethylene oxide very reactive. It’s commonly used in the production of ethylene glycol, a precursor for many chemical compounds.

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Most popular questions from this chapter

Draw structures for the following compounds: (a) 1,4-butanediol (b) 3 -amino-1-pentanol (c) cis-4-tert-butoxycyclohexanol (d) \(2,2,4,4\)-tetramethyl-3-pentanol (e) \((R)\)-sec-butyl alcohol (f) trans-3-chlorocyclohexanol (g) tert-butyl cyclopentyl ether

Draw structures for the following compounds: (a) \((R)-3\)-methyl-2-butanamine (b) cis-2-ethylcyclopentanamine (c) 1-hexanamine (d) 3 -methoxy-2-heptanamine (e) \(N\)-methyl-3-hexanamine (f) \((Z)-2\)-penten-2-amine

Draw \(N, N\)-dimethylethanamine clearly showing the threedimensional perspective at the nitrogen. Use the convention of solid and dashed wedges and include nitrogen's lone pair.

Draw structures for the following compounds: (a) 4-chloro- \(N\)-ethyl-2-butanamine (b) \((2 R, 3 R)-N\)-ethyl-2-methoxy- \(N\)-methyl-3-hexanamine (c) trans-2,3-epoxy-1-ethoxybutane (d) cis-3-aminocyclopentanol (e) \((2 R, 4 S)-4\)-chloro- \(N\)-phenyl-2-heptanamine

In contrast to simple amines, aziridines (three-membered rings containing a nitrogen) can often be separated into enantiomers. For example, the activation energy \(\left(\Delta G^{\frac{4}{*}}\right)\) for the inversion of \(1,2,2\)-trimethylaziridine is about \(18.5 \mathrm{kcal} / \mathrm{mol}(77.5 \mathrm{~kJ} / \mathrm{mol})\), much higher than that for simple amines. Explain.
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