1) The ¹H NMR spectra of carvone and the epoxidation product(s) are extremely complicated, so we've only given you partial spectra (from 8 3.0 -7.0 ppm), showing the double bond regions. There are three peaks in this region in the carvone spectrum, corresponding to H₂, Ho and H₂. Based on chemical shift or coupling considerations, assign the peaks for H₂ and Hbc (you can't distinguish between H, and Hc, so just label both peaks Hbic). H₂C He -CH₂ НЬ (D)-(+)-carvone H₂

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
Problem 66AP
icon
Related questions
Question
1) The ¹H NMR spectra of carvone and the epoxidation product(s) are extremely complicated, so
we've only given you partial spectra (from 8 3.0 -7.0 ppm), showing the double bond regions.
There are three peaks in this region in the carvone spectrum, corresponding to Ha, H, and H.
Based on chemical shift or coupling considerations, assign the peaks for H₂ and Hb/c (you can't
distinguish between H, and Hc, so just label both peaks Hbic).
H₂C
80
Transmittance [%]
30 40 50 60 70 80
6.8 6.6
******
¹H spectrum (partial) of (D)-(+)-carvone
¹H spectrum (partial) of unknown epoxidation product
6.8 6.6
6.4 6.2 6.0 5.8 5.6 5.4
6.2 6.0 5.8 5.6 5.4
✓ Carvone IR.jpg
BRUKER
3500
8895
***
He
3000
H₂₂
(D)-(+)-carvone
5.2
5.2
5.0 4.8
f1 (ppm)
2500
5.0
f1 (ppm)
Ha
-CH3
Ⓒ
4.6
2000
Wavenumber cm-1
4.6 4.4 4.2 4.0
4.2 4.0 3.8
1645.58-
1500
r
3.8
3.6
3.6
1000
3.4
S
3.4
3.2 3.0
3.2 3.0
500
Transcribed Image Text:1) The ¹H NMR spectra of carvone and the epoxidation product(s) are extremely complicated, so we've only given you partial spectra (from 8 3.0 -7.0 ppm), showing the double bond regions. There are three peaks in this region in the carvone spectrum, corresponding to Ha, H, and H. Based on chemical shift or coupling considerations, assign the peaks for H₂ and Hb/c (you can't distinguish between H, and Hc, so just label both peaks Hbic). H₂C 80 Transmittance [%] 30 40 50 60 70 80 6.8 6.6 ****** ¹H spectrum (partial) of (D)-(+)-carvone ¹H spectrum (partial) of unknown epoxidation product 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 6.2 6.0 5.8 5.6 5.4 ✓ Carvone IR.jpg BRUKER 3500 8895 *** He 3000 H₂₂ (D)-(+)-carvone 5.2 5.2 5.0 4.8 f1 (ppm) 2500 5.0 f1 (ppm) Ha -CH3 Ⓒ 4.6 2000 Wavenumber cm-1 4.6 4.4 4.2 4.0 4.2 4.0 3.8 1645.58- 1500 r 3.8 3.6 3.6 1000 3.4 S 3.4 3.2 3.0 3.2 3.0 500
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
General Physical Properties of Organic Compounds
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.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning