Question: Predict the products formed when ${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{-}\mathbf{C}\mathbf{\equiv }\overline{\mathbf{C}}\mathbf{:}{\mathbf{Na}}^{\mathbf{+}}$ reacts with the following compounds.

(a)ethyl bromide

(b)tert-butyl bromide

(c)formaldehyde

(d)cyclohexanone

(e)${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{CHO}$

(f)cyclohexanol

(g)butan-2-one,${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{COCH}}_{\mathbf{3}}$

The sodium salt that has four carbons in the parent chain with one triple bond and one negative charge on the carbon is but-1-yne-1-ide. This is an ionic species and is an anion because of the negative charge on the carbon atom. The carbon atom also has a lone pair of electrons.

The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with ethyl bromide result in the formation of hex-3-yne. The reaction is shown below.

The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with ethyl bromide

The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with tert-butyl bromide result in the formation of 2-methylprop-1-ene. The reaction is shown below.

The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with tert-butyl bromide

The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with formaldehyde result in the formation of pent-2-yn-1-ol. The reaction is shown below.

Reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with formaldehyde

The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with cyclohexanone result in the formation of 1-(but-1-yn-1-yl)cyclohexan-1-ol. The reaction is shown below.

Reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with cyclohexanone

The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$ result in the formation of oct-5-yn-4-ol. The reaction is shown below.

Reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$ with cyclohexanol result in the formation of oct-but-1-yne and sodium cyclohexanolate. The reaction is shown below

Reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with cyclohexanol

The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{COCH}}_3$ butan-2-one result in the formation of 3-methylhept-4-yn-3-ol. The reaction is shown below.

Reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2-\mathrm{C}\equiv \overline{\mathrm{C}}:{\mathrm{Na}}^{+}$with butan-2-one