An unknown compound of molecular formula C5H10O2, gives the HNMR data shown below. Which of the following structures is consistent with the data? **NMR Spectroscopy Analysis****Chemical Shift Data:**- A doublet at 1.23 ppm (6H)- A singlet at 2.10 ppm (3H)- A septet at 4.98 ppm (1H)**Possible Chemical Structures:**The provided chemical shift data corresponds to the following chemical structures:(a) **Structure A**- A molecule featuring a ketone (carbonyl group) with alkyl groups attached.(b) **Structure B**- Similar to Structure A, but the positioning of the alkyl groups differs, altering the chemical environment of the hydrogen atoms.(c) **Structure C**- This structure highlights an ester functional group with different alkyl chain attachments.(d) **Structure D**- Displaying a carboxylic acid functional group, showing variations in the hydrogen environment due to the presence of the hydroxyl group.(e) **Structure E**- Another ketone structure, but with an additional hydroxyl group (alcohol functional group) which affects the hydrogen placement and chemical shifts.**Explanation of Graphs/Diagrams:**The diagrams depict various organic molecules that could correspond to the observed NMR chemical shift data. Each molecule contains common functional groups such as esters, ketones, and carboxylic acids, with varying alkyl chain lengths and positions. These structural variations impact the hydrogen environments, thus affecting their NMR signals.The spectral data (doublet, singlet, septet) at specific ppm values help in identifying which of these structures matches the observed NMR signals, providing insights into the molecular structure and dynamics.**Educational Note:**Understanding NMR spectroscopy is crucial for identifying molecular structures and environments of hydrogen atoms in organic compounds. By analyzing chemical shifts, multiplicity (doublet, singlet, septet), and integrating with molecular structures, one can deduce the actual configurations of unknown compounds. This application is critical in organic chemistry, biochemistry, and pharmaceutical research for elucidating molecular structures.

Multiplicity in NMR for the signal (chemical shift) can be determined using the equation as follows:…

Answered: A doublet at 1.23 ppm (6H), a Singlet…

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A doublet at 1.23 ppm (6H), a Singlet at 2.10 (3H, and a Septet at 4.98 ppm (1H) (а) (b) (c) HO H. (d) (e)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

ChapterL4: Proton (1h) Nmr Spectroscopy

Section: Chapter Questions

Problem 21CTQ

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Mass Spectrometry

This process is an instrumental method in which a sample is changed to fast moving positive ions by electron bombardment. The charged particles vary due to their different mass to charge ratio and are estimated with the help of this difference. It is also called mass spectroscopy.

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An unknown compound of molecular formula C5H10O2, gives the HNMR data shown below. Which of the following structures is consistent with the data?

**NMR Spectroscopy Analysis**

**Chemical Shift Data:**
- A doublet at 1.23 ppm (6H)
- A singlet at 2.10 ppm (3H)
- A septet at 4.98 ppm (1H)

**Possible Chemical Structures:**

The provided chemical shift data corresponds to the following chemical structures:

(a) **Structure A**
- A molecule featuring a ketone (carbonyl group) with alkyl groups attached.

(b) **Structure B**
- Similar to Structure A, but the positioning of the alkyl groups differs, altering the chemical environment of the hydrogen atoms.

(c) **Structure C**
- This structure highlights an ester functional group with different alkyl chain attachments.

(d) **Structure D**
- Displaying a carboxylic acid functional group, showing variations in the hydrogen environment due to the presence of the hydroxyl group.

(e) **Structure E**
- Another ketone structure, but with an additional hydroxyl group (alcohol functional group) which affects the hydrogen placement and chemical shifts.

**Explanation of Graphs/Diagrams:**

The diagrams depict various organic molecules that could correspond to the observed NMR chemical shift data. Each molecule contains common functional groups such as esters, ketones, and carboxylic acids, with varying alkyl chain lengths and positions. These structural variations impact the hydrogen environments, thus affecting their NMR signals.

The spectral data (doublet, singlet, septet) at specific ppm values help in identifying which of these structures matches the observed NMR signals, providing insights into the molecular structure and dynamics.

**Educational Note:**

Understanding NMR spectroscopy is crucial for identifying molecular structures and environments of hydrogen atoms in organic compounds. By analyzing chemical shifts, multiplicity (doublet, singlet, septet), and integrating with molecular structures, one can deduce the actual configurations of unknown compounds. This application is critical in organic chemistry, biochemistry, and pharmaceutical research for elucidating molecular structures.

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