Question

Each of these compounds can be synthesized by an \(\mathrm{S}_{\mathrm{N}} 2\) reaction. Suggest a combination of haloalkane and nucleophile that will give each product. (a) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{SH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{PH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CN}\) (e) \(\mathrm{CH}_{3} \mathrm{SCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) (f) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{NH}^{+} \mathrm{Cl}^{-}\) (g) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{2} \mathrm{C}_{6} \mathrm{H}_{5}\) (h) \((R)-\mathrm{CH}_{3} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (i) \(\mathrm{CH}_{2}=\mathrm{CHCH}{ }_{2} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}\) (j) \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{OCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) (k) ClC1CCCCN1 (I) C1COCCO1

Short answer

Question: Suggest a combination of haloalkane and nucleophile that will yield the following products through an SN2 reaction: (a) CH3OCH3 (b) CH3SH (c) CH3CH2CH2PH2 (d) CH3CH2CN (e) CH3SCH2C(CH3)3 (f) (CH3)3NH+Cl- (g) C6H5COCH2C6H5 (h) (R)-CH3CHCH2CH2CH3 (i) CH2=CHCH2OCH(CH3)2 (j) CH2=CHCH2OCH2CH=CH2 (k) ClC1CCCCN1 (l) C1COCCO1 Answer: (a) CH3Cl and OCH3⁻ (b) CH3Cl and SH⁻ (c) CH3CH2CH2Cl and PH2⁻ (d) CH3CH2Cl and CN⁻ (e) CH3Cl and SCH2C(CH3)3⁻ (f) Cl(CH3)3 and NH3 (g) C6H5COCH2Cl and C6H5⁻ (h) (R)-CH3CHCH2CH2Cl and CH3⁻ (i) CH2=CHCH2Cl and OCH(CH3)2⁻ (j) CH2=CHCH2Cl and OCH2CH=CH2⁻ (k) ClC1CCCCCl and N1⁻ (l) C1COCCCl and O1⁻

Step-by-step solution

(a) CH3OCH3

For the synthesis of CH3OCH3, we can use the haloalkane CH3Cl and the nucleophile OCH3⁻.

(b) CH3SH

For the synthesis of CH3SH, we can use the haloalkane CH3Cl and the nucleophile SH⁻.

(c) CH3CH2CH2PH2

For the synthesis of CH3CH2CH2PH2, we can use the haloalkane CH3CH2CH2Cl and the nucleophile PH2⁻.

(d) CH3CH2CN

For the synthesis of CH3CH2CN, we can use the haloalkane CH3CH2Cl and the nucleophile CN⁻.

(e) CH3SCH2C(CH3)3

For the synthesis of CH3SCH2C(CH3)3, we can use the haloalkane CH3Cl and the nucleophile SCH2C(CH3)3⁻.

(f) (CH3)3NH+Cl-

For the synthesis of (CH3)3NH+Cl-, we can use the haloalkane Cl(CH3)3 and the nucleophile NH3.

(g) C6H5COCH2C6H5

For the synthesis of C6H5COCH2C6H5, we can use the haloalkane C6H5COCH2Cl and the nucleophile C6H5⁻.

(h) (R)-CH3CHCH2CH2CH3

For the synthesis of (R)-CH3CHCH2CH2CH3, we can use the haloalkane (R)-CH3CHCH2CH2Cl and the nucleophile CH3⁻.

(i) CH2=CHCH2OCH(CH3)2

For the synthesis of CH2=CHCH2OCH(CH3)2, we can use the haloalkane CH2=CHCH2Cl and the nucleophile OCH(CH3)2⁻.

(j) CH2=CHCH2OCH2CH=CH2

For the synthesis of CH2=CHCH2OCH2CH=CH2, we can use the haloalkane CH2=CHCH2Cl and the nucleophile OCH2CH=CH2⁻.

(k) ClC1CCCCN1

For the synthesis of ClC1CCCCN1, we can use the haloalkane ClC1CCCCCl and the nucleophile N1⁻.

(l) C1COCCO1

For the synthesis of C1COCCO1, we can use the haloalkane C1COCCCl and the nucleophile O1⁻.