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.
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.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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