Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

14. Compounds with Oxygen or Sulfur

Reactions of Thiols

GOB Chemistry

14. Compounds with Oxygen or Sulfur

Reactions of Thiols

Previous problemNext problem

Problem 53

Textbook Question

Oxidation of a dithiol such as 2,5-hexanedithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint: Draw the starting compound in line structure format first).

Verified step by step guidance

Start by understanding the structure of the starting compound, 2,5-hexanedithiol. This molecule consists of a six-carbon chain with thiol (-SH) groups attached to the second and fifth carbons. Draw this structure in a line structure format, where each vertex represents a carbon atom, and the thiol groups are shown as -SH.

Recognize that the oxidation of thiol groups (-SH) leads to the formation of a disulfide bond (-S-S-). In this reaction, the two sulfur atoms from the thiol groups will bond together, releasing two hydrogen atoms as part of the oxidation process.

To form the cyclic disulfide, connect the sulfur atoms from the thiol groups on the second and fifth carbons. This connection will create a six-membered ring, as the carbon chain loops back on itself to form a closed structure.

Redraw the structure to clearly show the six-membered ring. The ring will consist of four carbon atoms and two sulfur atoms, with the sulfur atoms connected by a disulfide bond (-S-S-). Ensure that all other bonds and hydrogens are correctly represented.

Double-check the structure to confirm that it satisfies the rules of valency for all atoms and that the disulfide bond is correctly incorporated into the six-membered ring. This is the final structure of the cyclic disulfide formed from the oxidation of 2,5-hexanedithiol.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Dithiol Compounds

Dithiols are organic compounds containing two thiol (-SH) groups. They are important in organic chemistry for their ability to undergo oxidation, leading to the formation of disulfides. In the case of 2,5-hexanedithiol, the two thiol groups are positioned on the first and fifth carbon atoms of a six-carbon chain, which is crucial for the subsequent cyclization reaction.

Oxidation Reaction

Oxidation is a chemical reaction that involves the loss of electrons or an increase in oxidation state. In the context of dithiols, oxidation leads to the formation of disulfides, where two thiol groups react to form a covalent bond between sulfur atoms. This process is essential for creating cyclic structures, such as the six-membered ring mentioned in the question.

Cyclic Disulfide Structure

A cyclic disulfide is a ring structure that contains a disulfide bond (–S–S–) as part of its framework. In the case of the oxidation of 2,5-hexanedithiol, the formation of a six-membered ring involves the two sulfur atoms from the thiol groups bonding together, resulting in a stable cyclic compound. Understanding the geometry and bonding in cyclic disulfides is key to drawing their correct structures.

Watch next

Master Thiol Redox Reaction Concept 1 with a bite sized video explanation from Jules

Start learning