Carboxylic Acids, Esters, Amines, and Amides

Draw the condensed structural formulas and write the IUPAC names for four structural isomers of the esters that have the molecular formula ${\mathrm{C}}_3{\mathrm{H}}_1{\mathrm{O}}_2·(14.3)$

The ester methyl butanoate has the odor and flavor of strawberries. $(14.3,14.4)$

a. Draw the condensed structural formula for methyl butanoate.

b. Write the IUPAC name for the carboxylic acid and the alcohol used to prepare methyl butanoate.

c. Write the balanced chemical equation for the acid hydrolysis of methyl butanoate.

Methyl benzoate, which smells like pineapple guava, is used to train detection dogs. (14.3, 14.4)

a. Draw the line-angle formula for methyl benzoate.

b. Write the IUPAC name for the carboxylic acid and alcohol used to prepare methyl benzoate.

c. Write the balanced chemical equation for the acid hydrolysis of methyl benzoate.

Phenylephrine is the active ingredient in some nose sprays used to reduce swelling of nasal membranes. 

Identify the functional groups in phenylephrine. $(14.1,14.3,14.5,14.6)$

Melatonin is a naturally occurring compound in plants and animals, where it regulates the biological time clock. 

Melatonin is sometimes used to counteract jet lag. Identify the functional groups in melatonin. $(14.1,14.3,14.5,14.6)$

There are four amine isomers with the molecular formula ${\mathrm{C}}_3{\mathrm{H}}_9 \mathrm{N}$. Draw their condensed structural formulas, write the common name, and classify each as a primary $\left(1°\right)$, secondary $\left(2°\right)$, or tertiary $\left(3°\right)$ amine. (14.5)

There are four amide isomers with the molecular formula ${\mathrm{C}}_3{\mathrm{H}}_7\mathrm{NO}$. Draw their condensed structural formulas and write the IUPAC name for each. (14.6)

Draw the condensed structural formulas for $\mathbf{a}$and $\mathbf{b}$and lineangle formulas for $\mathbf{c}$ and d:$(14.1,14.3)$

a. methyl acetate

b. 2,2 -dichlorobutanoic acid

c. 3-bromopentanoic acid

d. butyl benzoate

Write the IUPAC and common names, if any, for each of the following: $(14.1,14.3)$

Write the IUPAC and common names, if any, for each of the following: $(14.1,14.3)$

 Draw the condensed structural formulas for a and $\mathbf{b}$ and line angle formulas for $\mathrm{c}$and $\mathrm{d}$ :

a. pentyl formate

b. 5 -bromopentanoic acid

C. 3.5-dimethylhexanoic acid

d. butyl propanoate

Write the common name and classify each of the following compounds as primary $\left(1°\right)$ , secondary$\left(2°\right)$, or tertiary $\left(3°\right)$

a)     

b)

c)

Draw the condensed structural or line-angle formulas for the products of the following: 

a) 

b)

c)

d)

Write the common name and classify each of the following compounds as primary , secondary , or tertiary

a)

b)

c)

Draw the condensed structural or line-angle formulas for the products of the following: 

a)

b)

c)

Draw the condensed structural or line-angle formulas for the products of the following:

a)

b)

c)

 Condense the structural or line-angle formulas for the following products: 

a)

b)

c)

d)

Draw the condensed structural or line-angle formula if cyclic, for each of the following:

a. $dibutylamine$

b. $triethylamine$

c. $N,N-dipropylaniline$

d. $ethylmethylammonium bromide$

Draw the condensed structural or line-angle formulas for the products of the following: 

a.

b.

Draw the condensed structural or line-angle formulas for the products of the following: 

(a) ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{NH}}_2+{\mathrm{H}}_2\mathrm{O}\rightleftarrows$

(b)  ${\mathrm{CH}}_3-{\mathrm{CH}}_2-{\mathrm{NH}}_2+\mathrm{HCl}⟶$

Draw the condensed structural or line-angle formula if cyclic, for each of the following: 

a. $dimethylamine$

b. $cyclohexylamine$

c. $dimethylammonium chloride$

d. $N-propylaniline$

Voltaren is indicated for acute and chronic treatment of the symptoms of rheumatoid arthritis. Identify the functional groups in Voltaren. 

Draw the line-angle formula and write the IUPAC name for each of the following: 

a. A carboxylic acid that has the formula $C_6{H}_{12}{O}_2$, with no substituents

b. A carboxylic acid that has the formula $C_6{H}_{12}{O}_2$, with one ethyl substituent

4 Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following: (14.6)

Write the IUPAC name for each of the following: (14.6)

Write the IUPAC name for each of the following:

a.

b.

c.

Draw the line-angle formula and write the IUPAC name for each of the following: (14.1)

a. A carboxylic acid that has the formula ${\mathrm{C}}_3{\mathrm{H}}_{40}{\mathrm{O}}_2$, with no substituents

b. A carboxylic acid that has the formula ${\mathrm{C}}_3{\mathrm{H}}_{10}{\mathrm{O}}_2$, with two methyl substituents

Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following: (14.6)

Propyl acetate is the ester that gives the odor and smell of pears. 

a. Draw the condensed structural formula for propyl acetate.

b. Write the balanced chemical equation for the formation of propyl acetate.

c. Write the balanced chemical equation for the acid hydrolysis of propyl acetate.

d. Write the balanced chemical equation for the base hydrolysis of propyl acetate with $\mathrm{NaOH}$.

e. How many milliliters of a $0.208\mathrm{MNaOH}$ solution is needed to completely hydrolyze (saponify)

 $1.58 \mathrm{g}$of propyl   acetate?

Toradol is used in dentistry to relieve pain. Identify the functional groups in Toradol.

Ethyl octanoate is a flavor component of mangoes. 

1. Draw the condensed structural formula for ethyl octanoate.
2. Write the balanced chemical equation for the formation of ethyl octanoate.
3. Write the balanced chemical equation for the acid hydrolysis of ethyl octanoate.
4. Write the balanced chemical equation for the base hydrolysis of ethyl octanoate with $NaOH$.
5. How many milliliters of a $0.315 \mathrm{M} \mathrm{NaOH}$ solution is needed to completely hydrolyze (saponify) $2.84 \mathrm{g}$ of ethyl octanoate?

Novocain, a local anesthetic, is the ammonium salt of procaine. (14.5)

1. Draw the condensed structural formula for the ammonium salt (procaine hydrochloride) formed when procaine reacts with $\mathrm{HCl}$. (Hint: The tertiary amine reacts with HCl.)
2. Why is procaine hydrochloride used rather than procaine?

Lidocaine (xylocaine) is used as a local anesthetic and cardiac depressant. (14.5)

1. Draw the condensed structural formula for the ammonium salt formed when lidocaine reacts with $\mathrm{HCl}$.
2. Why is the ammonium salt of lidocaine used rather than the amine?