Draw the structure of a C5H100 (note the formula carefully) compoundi which gives a negative Jones (CrO3) test, does not decolorize Br2, and cannot be reduced with NaBt4.

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Chapter1: Chemical Foundations
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**Question 4:**

Draw the structure of a C₅H₁₀O (note the formula carefully) compound which gives a negative Jones (CrO₃) test, does not decolorize Br₂, and cannot be reduced with NaBH₄.

**Response Explanation:**

- **C₅H₁₀O**: The compound has five carbons, ten hydrogens, and one oxygen.

- **Negative Jones Test**: Indicates that the compound is likely not a primary or secondary alcohol or an aldehyde, as these would normally give a positive result (oxidation to a carboxylic acid).

- **Does Not Decolorize Br₂**: Suggests the absence of alkenes or alkynes, as these typically react with bromine.

- **Cannot be Reduced with NaBH₄**: Implies that the compound does not contain a reducible functional group like an aldehyde or ketone.

**Possible Structure:**

The diagram below the question shows a cyclic ether structure which aligns with a compound that meets these criteria. The depicted structure is a five-membered ring with an oxygen atom and appears to represent tetrahydropyran (also known as oxane), a type of cyclic ether.
Transcribed Image Text:**Question 4:** Draw the structure of a C₅H₁₀O (note the formula carefully) compound which gives a negative Jones (CrO₃) test, does not decolorize Br₂, and cannot be reduced with NaBH₄. **Response Explanation:** - **C₅H₁₀O**: The compound has five carbons, ten hydrogens, and one oxygen. - **Negative Jones Test**: Indicates that the compound is likely not a primary or secondary alcohol or an aldehyde, as these would normally give a positive result (oxidation to a carboxylic acid). - **Does Not Decolorize Br₂**: Suggests the absence of alkenes or alkynes, as these typically react with bromine. - **Cannot be Reduced with NaBH₄**: Implies that the compound does not contain a reducible functional group like an aldehyde or ketone. **Possible Structure:** The diagram below the question shows a cyclic ether structure which aligns with a compound that meets these criteria. The depicted structure is a five-membered ring with an oxygen atom and appears to represent tetrahydropyran (also known as oxane), a type of cyclic ether.
Expert Solution
Step 1

Jones test is test for detection of alcohols , only primary , secondary alcohols gives positive jones test. Tertiary alcohols and other functional groups gives negative jones test .

Br2 test is used for detection of saturation and unsaturation. Decolorize Br2 indicates presence of C=C . 

NaBH4 is reducing agent and reduces ketone to secondary alcohol and aldehyde to primary alcohol. 

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