Alcohols, Thiols, Ethers, Aldehydes, and Ketones

Which of the following will give a positive Tollens' test?

a. propanal 

b. ethanol 

c. ethyl methyl ether

Which compound in each pair would be more soluble in water? Explain. ($12.2$)

a. $bu\tan e$ or $1-propanol$

b. $2-propanol$ or $diethyl ether$

c. $ethanol$ or $1-hexanol$

Give the IUPAC name for each of the following: ($12.3$)

a.

b.

c. 

Draw the condensed structural or line-angle formula for the alcohol produced when hydrogen and a nickel catalyst reduce each of the following: ($12.4$)

a.

b.

c.

Draw the condensed structural or line-angle formula for the alcohol produced when hydrogen and a nickel catalyst reduce each of the following: ($12.4$)

a.

b.

c. 

Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions: ($12.4$)

a.

b.

c. 

d. 

Which compound in each pair would be more soluble in water? Explain. ($12.2$)

a. $ethane$ or $ethanol$

b. $2-propanol$ or $2-pen\tan ol$

c. $methyl propyl ether$ or $1-bu\tan ol$

Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions: (12.4)

a.

b. 

c. 

d.

A compound with the formula $C_4{H}_{8}O$ is synthesized from $2-methy-1-propanol$ and oxidizes easily to give a carboxylic acid. Draw the condensed structural formula and give the IUPAC name for the compound.

A compound with the formula $C_5{H}_{10}O$ oxidizes to give $3-pen\tan one$. Draw the condensed structural formula and give the IUPAC name for the compound.

Draw the condensed structural formulas and give the IUPAC name for all the alcohols that have the formula $C_5{H}_{12}O$.$\left(12.1\right)$

Draw the condensed structural or line-angle formula for the ketone or carboxylic acid product when each of the following is oxidized:$\left(12.4\right)$

a.

b. 

c.

d.

Compound $A$ is a primary alcohol whose formula is $C_3{H}_{8}O$. When compound $A$ is heated with strong acid, it dehydrates to form compound $B\left(C_3{H}_6\right)$. When compound $A$ is oxidised, compound $C\left(C_3{H}_{6}O\right)$ forms. Draw the condensed structural formulas and give the IUPAC names for compounds $A, B and C$.

Compound $X$ is a secondary alcohol whose formula is $C_3{H}_{8}O$. When compound $X$ is heated with strong acid, it dehydrates to form compound $Y\left(C_3{H}_6\right)$. When compound $X$ is oxidized, compound $Z\left(C_3{H}_{6}O\right)$ forms, which cannot be oxidized further. Draw the condensed structural formulas and give the IUPAC names for the compounds $X, Y and Z$.

Draw the condensed structural formulas and give the IUPAC names for all the aldehydes and ketones that have the formula ${\mathrm{C}}_5{\mathrm{H}}_{10}\mathrm{O}$.$\left(12.3\right)$

Draw the condensed structural or line-angle formula for the ketone or carboxylic acid product when each of the following is oxidized: $(12.4)$

a.

b. 

c.

d.

A metal (M) completely reacts with $34.8 mL$ of a $0.520 M$ $HCl$ solution to form $MC{l}_3$ and $H_2$.

a. Write the balanced chemical equation for the reaction of the metal and $HCl$ 

b. What volume, in milliliters, of $H_2$ produced at STP?

c. How many moles of metal M reacted?

d. If the metal has a mass of $0.420 g$, use your results from part c to determine the molar mass of the metal M.

e. What are the name and symbol of metal M in part d?

f.  Write the balanced chemical equation using the symbol of the metal from part e. 

 In a teaspoon $5 mL$ of a common liquid antacid, there are
$400 mg$ of $Mg{\left(OH\right)}_2$ and $400 mg$ of $Al{\left(OH\right)}_3$. A $0.080 M$$HCl$ solution, which is similar to stomach acid, is used to
neutralize $5.0 mL$ of the liquid antacid.

a. Write the balanced chemical equation for the neutralization
of $HCl$  and $Mg{\left(OH\right)}_2$
b. Write the balanced chemical equation for the neutralization
of $HCl$ and $Al{\left(OH\right)}_3$
c. What is the pH of the $HCl$ solution?
d. How many milliliters of the $HCl$ solution are needed to
neutralize the $Mg{\left(OH\right)}_2$?
e. How many milliliters of the $HCl$ solution are needed to
neutralize the $Al{\left(OH\right)}_3$?

Acetone (propanone), a clear liquid solvent with an acrid odor, is used to remove nail polish, paints, and resins. It has a low boiling point and is highly flammable. Acetone has a density of $0.786 g/mL$. Acetone is a solvent used in nail polish remover.

1.  What is the molecular formula of acetone? 
2. What is the molar mass of acetone? 
3.  Identify the bonds $\mathrm{C}-\mathrm{C} , \mathrm{C}-\mathrm{H}, \mathrm{C}-\mathrm{O}$ in a molecule of acetone as polar covalent or nonpolar covalent.
4.  Write the balanced chemical equation for the combustion of acetone.
5.  How many grams of oxygen gas are needed to react with $15 mL$of acetone? 

One of the components of gasoline is octane, ${\mathrm{C}}_8{\mathrm{H}}_{18}$, which has a density of $0.803 g/mL$. The combustion of $1$ mole of octane provides $5510 kJ$. A hybrid car has a fuel tank with a capacity of $11.9 gal$ and a gas mileage of $45 mi/gal$

1.   Write the balanced chemical equation for the combustion of octane. 
2.  Is the combustion of octane endothermic or exothermic? 
3.  How many moles of octane are in one tank of fuel, assuming it is all octane? 
4.  If the total mileage of this hybrid car for one year is $24500 mi$, how many kilograms of carbon dioxide would be produced from the combustion of the fuel, assuming it is all octane? 

 Butyraldehyde is a clear liquid solvent with an unpleasant odor. It has a low boiling point and is highly flammable. Butyraldehyde has a density of $0.802 gm/mL$. The unpleasant odor of old gym socks is due to butyraldehyde.

1. . Draw the condensed structural formula for butyraldehyde.
2. Draw the line-angle formula for butyraldehyde
3.  What is the IUPAC name of butyraldehyde?
4.  Draw the condensed structural formula for the alcohol that is produced when butyraldehyde is reduced.
5.  Write the balanced chemical equation for the complete combustion of butyraldehyde.
6.  How many grams of oxygen gas are needed to completely react with 15.0 mL of butyraldehyde?
7.  How many liters of carbon dioxide gas are produced at STP from the reaction in part f? 

Ionone is a compound that gives violets their aroma. The small, edible, purple flowers of violets are used in salads and to make teas. Liquid ionone has a density of

$0.935 g/mL$

a. What functional groups are present in ionone?

 b. Is the double bond on the side chain cis or trans? 

c. What are the molecular formula and molar mass of ionone? 

d. How many moles are in $2.00 mL$ of ionone ?

e. When ionone reacts with hydrogen in the presence of a platinum catalyst, hydrogen adds to the double bonds and converts the ketone group to an alcohol. Draw the condensed structural formula and give the molecular formula for the product. 

f. How many milliliters of hydrogen gas at STP are needed to completely react with $5.00 mL$ of ionone?