Non Equivalent Protons and Molecular Ion Discussion

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Question Description

Assignment
  1. For this discussion, you are asked once again to select organic compound from your text book or one that you found on the list of ingredients from a product in your home or select your favorite organic compound. No ionic compounds!
  2. The compound of your choice must be an organic compound. Please make sure you are able to answer the following questions regarding the compound of your choice. You may have difficulty answering the questions below if your compound of choice is complex. In this case, the simpler the better. In order to earn full credit, you must clearly label all protons and carbon atoms in your structure.
  3. Using your knowledge or the material covered in Weeks 1 – 6, your text books and the Internet answer the following questions regarding your compound.
    1. What is the name and structure of your compound? Please be sure to include the structure of your compound and not just the molecular formula.
    2. What is the major function group in your compound (Hint: Look at the ending of the name of your compound for a hint).
    3. List all of the other functional groups present in your compound.
    4. What is the HDI (Hydrogen Deficiency Index) for your compound?
    5. How many sets of non-equivalent protons are present in your compound?
    6. Please label all protons in your structure and indicate what would be the multiplicity of each set of non-equivalent protons in your compound (singlet, doublet, etc.)?
    7. How many peaks would you predict would appear in the Carbon-13 NMR spectrum? Please label all carbons in your structure.
    8. Which carbon atom in your compound would you predict would be the farthest downfield in your C-13 Spectrum?
    9. Pick at least two functional groups present in your compound and describe where they would appear in the IR spectrum of this compound. Please be sure to include the actual absorption frequencies in your discussion posting.
    10. What would be the m/z value for the molecular ion peak of your compound? Remember m/z values are whole numbers.
  4. Remember to site your sources in AMA style. Anything you post has to be rewritten in your own words. Do not cut and paste from another source and claim it as your own. Any posting that contains information word for word from another site will be considered to be plagiarized and will receive a grade of zero. Plagiarism is a violation of the Academic Integrity Statement and will be dealt with on an individual basis.
  5. Respond to at least two other students.
  6. Contribute to an ongoing discussion by responding to comments made to your posting or to comments made by other students to other postings.
No plagiarism. Please answer in your own words.

Tutor Answer

proggerardo
School: Duke University

Attached you will find the answers for the discussion. Please let me know if you need edits 😊

ANSWERS. ORGANIC CHEMISTRY DISCUSSION.
1. Compound name and structure (1)
IUPAC name: N,N-Diethyl-3-methylbenzamide or N,N-Diethyl-m-toluamide (also known as DEET).

O
N

2. Major functional group (1):
Tertiary amide.
3. Others functional groups (1):
Arene (Aromatic ring).
4. IHD (1)
𝐢12 𝐻17 𝑁𝑂 ≑ 𝐢13 𝐻18
𝐼𝐻𝐷 =

2(13) + 2 βˆ’ 18 28 βˆ’ 18
=
=5
2
2

5. How many sets of non-equivalent protons? (2)
There are seven sets of non-equivalent protons present in DEET.

O
F

C

E
G

N
B

D
A

E

G

6. Multiplicity of protons (2).
β€’ Signal A (7.25 ppm): Triplet (part of aromatic multiplet).
β€’ Signal B (7.19 ppm): Doublet (part of aromatic multiplet).
β€’ Signal C (7.18 ppm): Singlet (part of aromatic multiplet).
β€’ Signal D (7.12 ppm): Doublet (part of aromatic multiplet).
β€’ Signal E (3.40 ppm): Quadruplet (multiplet).
β€’ Signal F (2.36 ppm): Singlet.
β€’ Signal G (1.165 ppm):...

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