Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 1) Li—= 2) H3O+ C5H8O 2 3
Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 1) Li—= 2) H3O+ C5H8O 2 3
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 45MP
Related questions
Question
![Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a
synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to
give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a
mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a
Grignard reagent.)
1
13.17 a
1) Li—=
2) H₂O+
нас!!!!!!
C5H8O
Edit Drawing
2
Ž
Modify the given structure of the starting material to draw the major product.
an
3](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4193e74f-1c62-4d29-b274-86bdf2d18bcf%2Ff7be7508-2d6f-42db-bf72-d96162090cce%2F9i87btb_processed.png&w=3840&q=75)
Transcribed Image Text:Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a
synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to
give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a
mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a
Grignard reagent.)
1
13.17 a
1) Li—=
2) H₂O+
нас!!!!!!
C5H8O
Edit Drawing
2
Ž
Modify the given structure of the starting material to draw the major product.
an
3
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
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!
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 2 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
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.Recommended textbooks for you
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)