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ducing agent, imines NEt NHẸt -H2O EINH, + HC—C—СH, H3C-C-CH3 H, Pt 30 psi ELOH H,C-CH-CH3 (23.22) an imine (not isolated) acetone ethylisopropylamine Reduction of the C=N double bond is analogous to reduction of the C=0 double bond (Sec. 19.8). Notice that thhe imine or enamine does not have to be isolated, but is reduced within the reaction mixture as it forms. Because imines and enamines are reduced more rapidly than carbonyl compounds, reduction of the carbonyl compound is not a competing reaction. PROBLEM 25.14 Provide a reaction mechanism for step 1, formation of the imine, in Eq. 23.22 (Hint: Refer to Sec. 19.11A).

ducing agent, imines NEt NHẸt -H2O EINH, + HC—C—СH, H3C-C-CH3 H, Pt 30 psi ELOH H,C-CH-CH3 (23.22) an imine (not isolated) acetone ethylisopropylamine Reduction of the C=N double bond is analogous to reduction of the C=0 double bond (Sec. 19.8). Notice that thhe imine or enamine does not have to be isolated, but is reduced within the reaction mixture as it forms. Because imines and enamines are reduced more rapidly than carbonyl compounds, reduction of the carbonyl compound is not a competing reaction. PROBLEM 25.14 Provide a reaction mechanism for step 1, formation of the imine, in Eq. 23.22 (Hint: Refer to Sec. 19.11A).

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23.14
23.8 HOFMANN ELIMINATION OF QUATERNARY A 12 21 Continue the sequence of reactions in Eqs. 23.16a-c to show how trimethylammonium ioc in Eq. 23.15. 23,22 Outline a preparation of each of the following from an amine and an acid chloride. (a) N-phenylbenzamide (b) N-benzyl-N-ethylpropanamide 23.8 HOFMANN ELIMINATION OF QUATERNARY AMMONIUM HYDROXIDES The previous section discussed ways to make carbon-nitrogen bonds. In these reacti anines react as nucleophiles. The subject of this section is an elimination reaction use oreak carbon-nitrogen bonds. In this reaction, which involves quaternary ammonium hya ues (R,N* ¯OH) as starting materials, amines act as leaving groups. When a quaternary ammonium hydroxide is heated, a B-elimination reaction t. e to give an alkene, which distills from the reaction mixture. CH2 NME3 NMe, -CH, + H-—ОН heat trimethylamine H. FHO- a quaternary ammonium hydroxide methylenecyclohexane (74% yield)
Transcribed Image Text:23.8 HOFMANN ELIMINATION OF QUATERNARY A 12 21 Continue the sequence of reactions in Eqs. 23.16a-c to show how trimethylammonium ioc in Eq. 23.15. 23,22 Outline a preparation of each of the following from an amine and an acid chloride. (a) N-phenylbenzamide (b) N-benzyl-N-ethylpropanamide 23.8 HOFMANN ELIMINATION OF QUATERNARY AMMONIUM HYDROXIDES The previous section discussed ways to make carbon-nitrogen bonds. In these reacti anines react as nucleophiles. The subject of this section is an elimination reaction use oreak carbon-nitrogen bonds. In this reaction, which involves quaternary ammonium hya ues (R,N* ¯OH) as starting materials, amines act as leaving groups. When a quaternary ammonium hydroxide is heated, a B-elimination reaction t. e to give an alkene, which distills from the reaction mixture. CH2 NME3 NMe, -CH, + H-—ОН heat trimethylamine H. FHO- a quaternary ammonium hydroxide methylenecyclohexane (74% yield)
+ HI (23.21) Eqs. 23.19 and 23.21) is called exhaustive methylation. imines and enamines, respectively (Sec. 19.11). In the presence of a reducing agent, imines When primary and secondary amines react with either aldehydes or ketones, they form Conversion of an amine into a quaternary ammonium salt with excess methyl iodide (as in CH;CH3 sec-butyltrimethylammonium sec-butylmethylamine iodide B. Reductive Amination and enamines are reduced to amines. NEt NHE. -H2O H2, Pt 30 psi ELOH E:NH2 + H3C-C-CH3 H3C-C-CH3 H;C-CH-CH3 (23.22) an imine (not isolated) acetone ethylisopropylamine Reduction of the C=N double bond is analogous to reduction of the C=0 double bond (Sec. 19.8). Notice that te imine or enamine does not have to be isolated, but is reduced within the reaction mixture as it forms. Because imines and enamines are reduced more rapidly than carbonyl compounds, reduction of the carbonyl compound is not a competing reaction. PROBLEM 23.14 Provide a reaction mechanism for step 1, formation of the imine, in Eq. 23.22 (Hint: Refer to Sec. 19.11A).
Transcribed Image Text:+ HI (23.21) Eqs. 23.19 and 23.21) is called exhaustive methylation. imines and enamines, respectively (Sec. 19.11). In the presence of a reducing agent, imines When primary and secondary amines react with either aldehydes or ketones, they form Conversion of an amine into a quaternary ammonium salt with excess methyl iodide (as in CH;CH3 sec-butyltrimethylammonium sec-butylmethylamine iodide B. Reductive Amination and enamines are reduced to amines. NEt NHE. -H2O H2, Pt 30 psi ELOH E:NH2 + H3C-C-CH3 H3C-C-CH3 H;C-CH-CH3 (23.22) an imine (not isolated) acetone ethylisopropylamine Reduction of the C=N double bond is analogous to reduction of the C=0 double bond (Sec. 19.8). Notice that te imine or enamine does not have to be isolated, but is reduced within the reaction mixture as it forms. Because imines and enamines are reduced more rapidly than carbonyl compounds, reduction of the carbonyl compound is not a competing reaction. PROBLEM 23.14 Provide a reaction mechanism for step 1, formation of the imine, in Eq. 23.22 (Hint: Refer to Sec. 19.11A).
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