Which of the following compounds are chiral? Draw each compound in its most symmetric con- formation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer. (a) meso-2,3-dibromo-2,3-dichlorobutane (b) (±)-2,3-dibromo-2,3-dichlorobutane (c) (2R,3S)-2-bromo-3-chlorobutane (d) (2R,3S)-2,3-dibromobutane (e) (R, R)-2,3-dibromobutane (1) CHO H -OH -H CH₂OH HO H Br H CH, H CH₂ H - Br (h) H Br CH, H H CH₂ H Br

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**Problem 5-21**

**Objective:** Identify which of the following compounds are chiral. Draw each compound in its most symmetric conformation, mark (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

**Compounds to Analyze:**
(a) meso-2,3-dibromo-2,3-dichlorobutane  
(b) (±)-2,3-dibromo-2,3-dichlorobutane  
(c) (2R,3S)-2-bromo-3-chlorobutane  
(d) (2R,3S)-2,3-dibromobutane  
(e) (R,R)-2,3-dibromobutane  

**References:**
- Diagrams (f), (g), and (*h) are provided below descriptions.
  
**Diagram Descriptions:**

- Diagram (f): A Fischer projection of a sugar with an aldehyde group (CHO) at the top, two hydroxyl groups (OH) on the left and right on the second carbon, and a CH₂OH group at the bottom. This structure is a typical projection to illustrate stereochemistry in sugars.
  
- Diagram (g): A chair conformation showing multiple carbon atoms with hydrogen and methyl (CH₃) groups attached. There are bromine (Br) atoms shown on some carbon positions. This representation helps visualize the spatial arrangement in cyclohexane derivatives.
  
- Diagram (*h): Another chair conformation, similar to diagram (g), highlighting specific carbon atoms with bromine (Br) and methyl (CH₃) groups, indicating asymmetric centers with an asterisk (*). This emphasizes the analysis of chirality and mirror symmetry in the cyclic structure.
Transcribed Image Text:**Problem 5-21** **Objective:** Identify which of the following compounds are chiral. Draw each compound in its most symmetric conformation, mark (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer. **Compounds to Analyze:** (a) meso-2,3-dibromo-2,3-dichlorobutane (b) (±)-2,3-dibromo-2,3-dichlorobutane (c) (2R,3S)-2-bromo-3-chlorobutane (d) (2R,3S)-2,3-dibromobutane (e) (R,R)-2,3-dibromobutane **References:** - Diagrams (f), (g), and (*h) are provided below descriptions. **Diagram Descriptions:** - Diagram (f): A Fischer projection of a sugar with an aldehyde group (CHO) at the top, two hydroxyl groups (OH) on the left and right on the second carbon, and a CH₂OH group at the bottom. This structure is a typical projection to illustrate stereochemistry in sugars. - Diagram (g): A chair conformation showing multiple carbon atoms with hydrogen and methyl (CH₃) groups attached. There are bromine (Br) atoms shown on some carbon positions. This representation helps visualize the spatial arrangement in cyclohexane derivatives. - Diagram (*h): Another chair conformation, similar to diagram (g), highlighting specific carbon atoms with bromine (Br) and methyl (CH₃) groups, indicating asymmetric centers with an asterisk (*). This emphasizes the analysis of chirality and mirror symmetry in the cyclic structure.
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