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6.21 Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction. $CH_2=CH-CH-CH_3 + Na^+OCH_3 \xrightarrow{CH_3OH} CH_2=CH-CH-CH_3$ $\qquad \quad \mid \quad \qquad \mid$ $\qquad Br \qquad \qquad OCH_3$ $CH_2=CH-CH-CH_3 + CH_3OH \longrightarrow CH_2=CH-CH-CH_3 + CH_3CH=CHCH_3$ $\qquad \quad \mid \qquad \qquad \mid \qquad \mid$ $\qquad Br \qquad \qquad OCH_3 \qquad OCH_3$ Nucleophilic Substitution and Elimination Reactions in Organic Synthesis

          6.21 Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction.

$CH_2=CH-CH-CH_3 + Na^+OCH_3 \xrightarrow{CH_3OH} CH_2=CH-CH-CH_3$
$\qquad \quad \mid \quad \qquad \mid$
$\qquad Br \qquad \qquad OCH_3$

$CH_2=CH-CH-CH_3 + CH_3OH \longrightarrow CH_2=CH-CH-CH_3 + CH_3CH=CHCH_3$
$\qquad \quad \mid \qquad \qquad \mid \qquad \mid$
$\qquad Br \qquad \qquad OCH_3 \qquad OCH_3$

Nucleophilic Substitution and Elimination Reactions in Organic Synthesis

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6.21 Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction.

CH2=CH-CH-CH3 + Na^+OCH3 CH3OH CH2=CH-CH-CH3
| |
Br OCH3

CH2=CH-CH-CH3 + CH3OH ⟶ CH2=CH-CH-CH3 + CH3CH=CHCH3
| | |
Br OCH3 OCH3

Nucleophilic Substitution and Elimination Reactions in Organic Synthesis

Added by Jessica F.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

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Solved by Expert Sri K

03/27/2023

Step 1

The nucleophile is the methoxide ion (OCH$_3^-$). The methoxide ion attacks the carbon atom that is bonded to the bromine atom. The bromine atom leaves as a bromide ion (Br$^-$). The product of this reaction is an ether. Show more…

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6.21 Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction. CH$_2$=CH-CH-CH$_3$ + Na$^+$OCH$_3$ Br CH$_2$OH CH$_2$=CH-CH-CH$_3$ OCH$_3$ CH$_2$=CH-CH-CH$_3$ + CH$_3$OH $\longrightarrow$ CH$_2$=CH-CH-CH$_3$ + CH$_2$CH=CHCH$_3$ Br OCH$_3$ OCH$_3$ Nucleophilic Substitution and Elimination Reactions in Organic Synthesis

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