Question

Devise a synthesis of each substituted cyclopropane. Use acetylene (HC≡CH) as a starting material in part...

Devise a synthesis of each substituted cyclopropane. Use acetylene (HC≡CH) as a starting material in part (a), and cyclohexanone as a starting material in part (b). You may use any other organic compounds and any needed reagents.

a.


b.

0 0
Add a comment Improve this question Transcribed image text
Answer #1

a.

Sodium amide abstracts a proton from acetylene to form acetylide anion which then attacks the carbon atom bearing bromine atom to give substituted alkyne.

Acetylene proton is abstracted by base sodium amide to give acetylide anion which then attacks the carbon atom bearing bromine atom to give substituted alkyne.

Alkyne is reduced to cis-alkene by treating the alkyne with in the presence of Lindlar’s catalyst.

Alkene reacts with in the presence of to give the desired product.

b.

Cyclohexanone reacts with bromine in the presence of acetic acid to give 2-bromocyclohexanone.2-bromocyclohexanone reacts with strong base to give unsaturated carbonyl compound.

Dimethyl lithium cuprate reacts with cyclohex-2-enone to give 3-methyl-cyclohexanone.

The compound, 3-methyl-cyclohexanone reacts with to give 1-methyl-3-methylenecyclohexane.1-methyl-3-methylenecyclohexane reacts with chloroform in the presence of strong base to give 1,1-dichloro-5-methylspiro[2.5]octane.

The compound, 1,1-dichloro-5-methylspiro[2.5]octane reacts with dimethyl lithium cuprate to give desired product.

Add a comment
Know the answer?
Add Answer to:
Devise a synthesis of each substituted cyclopropane. Use acetylene (HC≡CH) as a starting material in part...
Your Answer:

Post as a guest

Your Name:

What's your source?

Earn Coins

Coins can be redeemed for fabulous gifts.

Not the answer you're looking for? Ask your own homework help question. Our experts will answer your question WITHIN MINUTES for Free.
Similar Homework Help Questions
ADVERTISEMENT
Free Homework Help App
Download From Google Play
Scan Your Homework
to Get Instant Free Answers
Need Online Homework Help?
Ask a Question
Get Answers For Free
Most questions answered within 3 hours.
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT