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Which of the following primary amines cannot be made by the given synthetic sequences? R's can be hydrogen if needed. Assume any necessary workup. Answers may be repeated. NH2 a NH2 d NH2 NH2 v Choose... b NH3 HO CF3 a and d band c R R' NaBH3CN all of the amines can be synthesized c and d NH3 LIAIH4 a .R HO, DCC a and b b and d a and c 9.

Which of the following primary amines cannot be made by the given synthetic sequences? R's can be hydrogen if needed. Assume any necessary workup. Answers may be repeated. NH2 a NH2 d NH2 NH2 v Choose... b NH3 HO CF3 a and d band c R R' NaBH3CN all of the amines can be synthesized c and d NH3 LIAIH4 a .R HO, DCC a and b b and d a and c 9.

Chemistry
Chemistry
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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
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### Primary Amines Synthesis #### Problem Statement Identify which of the following primary amines cannot be synthesized using the given synthetic sequences. Note that "R's" can be hydrogen if needed, and any necessary workup is assumed. The answers might be repeated. #### Amines - **a**: ``` CH3-CH2-C(NH2)-CH3 ``` - **b**: ``` NH2 | CH3-CH-CH3 ``` - **c**: ``` CH3-CH2-CH2-NH2 ``` - **d**: ``` CH3-CH3 | NH2 ``` #### Synthetic Sequences The two given synthetic sequences involve: 1. **Sequence 1**: - Starting material: ``` R-C=O ``` - Reagents: ``` NH3, HO-CF3, NaBH3CN ``` - Product: ``` R'-NH2 ``` This sequence represents reductive amination where a carbonyl compound (R-C=O) is converted into a primary amine (R'-NH2) using ammonia (NH3), a cyanoborohydride (NaBH3CN) as a reducing agent, and trifluoroacetic acid (HO-CF3) to stabilize intermediates. 2. **Sequence 2**: - Starting material: ``` R-C=O ``` - Reagents: ``` NH3, DCC, LiAlH4 ``` - Product: ``` R'-NH2 ``` This sequence depicts another method for reducing a carbonyl compound to a primary amine using ammonia (NH3), dicyclohexylcarbodiimide (DCC) as an activator, and lithium aluminum hydride (LiAlH4) as a reducing agent. #### Multiple Choice Options The multiple-choice options provided to the student are: - a and d - b and c - all of the amines can be synthesized - c and d - a - a and b - a and d - a and c - none of the amines can be synthesized - d ####
Transcribed Image Text:### Primary Amines Synthesis #### Problem Statement Identify which of the following primary amines cannot be synthesized using the given synthetic sequences. Note that "R's" can be hydrogen if needed, and any necessary workup is assumed. The answers might be repeated. #### Amines - **a**: ``` CH3-CH2-C(NH2)-CH3 ``` - **b**: ``` NH2 | CH3-CH-CH3 ``` - **c**: ``` CH3-CH2-CH2-NH2 ``` - **d**: ``` CH3-CH3 | NH2 ``` #### Synthetic Sequences The two given synthetic sequences involve: 1. **Sequence 1**: - Starting material: ``` R-C=O ``` - Reagents: ``` NH3, HO-CF3, NaBH3CN ``` - Product: ``` R'-NH2 ``` This sequence represents reductive amination where a carbonyl compound (R-C=O) is converted into a primary amine (R'-NH2) using ammonia (NH3), a cyanoborohydride (NaBH3CN) as a reducing agent, and trifluoroacetic acid (HO-CF3) to stabilize intermediates. 2. **Sequence 2**: - Starting material: ``` R-C=O ``` - Reagents: ``` NH3, DCC, LiAlH4 ``` - Product: ``` R'-NH2 ``` This sequence depicts another method for reducing a carbonyl compound to a primary amine using ammonia (NH3), dicyclohexylcarbodiimide (DCC) as an activator, and lithium aluminum hydride (LiAlH4) as a reducing agent. #### Multiple Choice Options The multiple-choice options provided to the student are: - a and d - b and c - all of the amines can be synthesized - c and d - a - a and b - a and d - a and c - none of the amines can be synthesized - d ####
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