Amphetamine is a powerful stimulant of the central nervous system.

(a) Which proton in amphetamine is most acidic?

(b) What products are made when amphetamine is treated with NaH?

(c) What products are made when amphetamine is treated with HCI?

Propranolol is an antihypertensive agent-that is, it lowers blood pressure.

(a) Which proton in propranolol is most acidic?

(b) What products are made when propranolol is treated with NaH?

(c) Which atom is most basic?

(d) What products are made when propranolol is treated with HCI?

Label the Lewis acid and base. Use curved arrow notation to show the movement of electron pairs.

$$CH_2 = \underset{H}{\underset{|}{\overset{CH_2}{\overset{|}{C}}}} + H_3{\overset{\large \sdot\sdot}{O^{+}}} \longrightarrow CH_3 - \underset{H}{\underset{|}{\overset{CH_3}{\overset{|}{C^{+}}}}} + H_2\overset{\large\sdot\sdot}{O:}$$

Draw the product formed when

$$\left( \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \right) _ { 3 } \mathrm { N } :,$$

a Lewis base, reacts with each Lewis acid:

$$(\mathrm { a } ) \mathrm { B } \left( \mathrm { CH } _ { 3 } \right) _ { 3 }; \quad (b)\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { C } ^ { + } ; \quad ( \mathrm { c } ) \mathrm { AlCl } _ { 3 }.$$

Draw the products of each reaction, and label the nucleophile and electrophile.

a. $CH_3CH_2-\overset{\large\sdot\sdot}{\underset{\large\sdot\sdot}{{O}}}-CH_2-CH_3 + BBr_3 \longrightarrow$

b. $CH_3 - \overset{:O:}{\overset{||}{C}} + AlCl_3$

Label the acid and base, and the conjugate acid and base in the following reactions. Use curved arrows to show the movement of electron pairs.

a. HCl + H$_2$O $\leftrightarrows$ Cl$^-$ + H$_3$O^{+}

b. $CH_3 - \overset{O}{\overset{||}{C}}-CH_3$ + $^{-}$OCH$_3$ $\leftrightarrows$ $CH_3 - \overset{O}{\overset{||}{C}}-\bar{C}H_3$ + CH$_3$OH

For each reaction, label the Lewis acid and base. Use curved arrow notation to show the movement of electron pairs.

a. BF$_3$ + CH$_3$ - $\overset{\large\sdot\sdot}{\underset{\large\sdot\sdot}{{O}}}$ - CH$_3$ $\longrightarrow$ $F-^{-}\underset{F}{\underset{|}{\overset{F}{\overset{|}{B}}}}-^{+}\underset{CH_3}{\underset{|}{\overset{CH_3}{\overset{|}{O:}}}}$

b. $\left({CH}_3\right)_2 \stackrel{+}{{C}} {H}+-{ }^{-} {OH} \longrightarrow\left({CH}_3\right)_2 {CHOH}$

Which compounds are Lewis acids?

$$\text { a. BBr}_3\quad \mathrm { b } . \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH }\quad \mathrm { c } . \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { C } ^ { + }\quad \text { d. Br }^-$$

Which compounds are Lewis bases?

$$\text { a. } \mathrm { NH } _ { 3 }\quad \mathrm { b } . \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }\quad \mathrm { c.H }^-\quad \mathrm { d } . \mathrm { H } - \mathrm { C } \equiv \mathrm { C } - \mathrm { H }$$

Compounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes. In which form will amphetamine pass through a cell membrane?

Draw the products formed when 2-propanol

$$[ ( \mathrm { CH } _ { 3 } ) _ { 2 } \mathrm { CHOH } ],$$

the main ingredient in rubbing alcohol, is treated with each acid or base:

$$\text { (a) } \mathrm { NaH } ; ( \mathrm { b } ) \mathrm { H } _ { 2 } \mathrm { SO } _ { 4 }; (\mathrm { c } ) \mathrm { Li } ^ { + - } \mathrm { N } [ \mathrm { CH } ( \mathrm { CH } _ { 3 } ) _ { 2 } ] _ { 2 }; \text { (d) } \mathrm { CH } _ { 3 } \mathrm { CO } _ { 2 } \mathrm { H }.$$

Study the diagram of the lac operon shown below. a. Explain the role of the following elements shown in the diagram: promoter, operator, and structural genes. b. What does it mean to say that a gene is turned "on"? c. Are the structural genes turned "on" in the diagram of the lac operon shown below?

Which proton in each of the following drugs is most acidic? THC is the active component in marijuana, and ketoprofen is an anti-inflammatory agent.

a. THC tetrahydrocannabinol b. ketoprofen

Rank the compounds in each group in order of increasing acidity.

$$\begin{array} {l} \mathrm { a } . \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }, \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH }, \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 } \\ \mathrm { b } . \mathrm { BrCH } _ { 2 } \mathrm { COOH }, \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { COOH }, \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } \\ \mathrm { c } . \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 },\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { N }, \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } \end{array}$$