Organic Chemistry

Write a condensed structural formula, such as\(C{H_3}C{H_3}\) , and describe the molecular geometry at each carbon atom.

(a) propene

(b) 1-butanol

(c) ethyl propyl ether

(d) cis-4-bromo-2-heptene

(e) \(2,2,3\) -trimethylhexane

(f) formaldehyde

Draw the skeletal structures for these two molecules

Identify the chemical formula of the molecule represented here:

Name the following molecule:

Name the following molecule:

Write the chemical formula and Lewis’s structure of the following, each of which contains five carbon atoms: (a) an alkane (b) an alkene (c) an alkyne

What is the difference between the hybridization of carbon atoms’ valence orbitals in saturated and unsaturated hydrocarbons?

On a microscopic level, how does the reaction of bromine with an alkene differ from its reaction with an alkyne? How are they similar?

Explain why unbranched alkenes can form geometric isomers while unbranched alkanes cannot. Does this explanation involve the macroscopic domain or the microscopic domain?

Explain why these two molecules are not isomers:

Explain why these two molecules are not isomers:

How does the carbon-atom hybridization change when polyethylene is prepared from ethylene?

Write the chemical formula, condensed formula, and Lewis structure for each of the following hydrocarbons:

(a) heptane

(b) 3-methylhexane

(c) trans-3-heptene

(d) 4-methyl-1-hexene

(e) 2-heptyne

(f) 3,4-dimethyl-1-pentyne

Give the complete IUPAC name for each of the following compounds:

Give the complete IUPAC name for each of the following compounds:

Butane is used as a fuel in disposable lighters. Write the Lewis structure for each isomer of butane.

Write Lewis structures and name the five structural isomers of hexane.

Write Lewis structures for the cis–trans isomers of \({\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{CH = CHCL}}\)

Write structures for the three isomers of the aromatic hydrocarbon xylene,\({C_6}{H_4}{\left( {C{H_3}} \right)_2}\)

Write two complete balanced equations for the following reaction, one using condensed formulas and one using Lewis structures.

Methyl amine is added to a solution of \(HCl.\) 

Isooctane is the common name of the isomer of \({C_8}{H_{18}}\) used as the standard of 100 for the gasoline octane rating:

(a) What is the IUPAC name for the compound?

(b) Name the other isomers that contain a five-carbon chain with three methyl substituents.

Write Lewis structures and IUPAC names for the alkyne isomers of \({C_4}{H_6}.\)

Write Lewis structures and IUPAC names for all isomers of \({C_4}{H_9}Cl.\)

Name and write the structures of all isomers of the propyl and butyl alkyl groups.

Write the structures for all the isomers of the \(--{C_5}{H_{11}}\) alkyl group.

Write Lewis structures and describe the molecular geometry of each carbon atom in the following compounds:

(a) cis-3-hexene

(b) cis-1-chloro-2-bromoethene

(c) 2-pentyne

(d) trans-6-ethyl-7-methyl-2-octene

Benzene is one of the compounds used as an octane enhancer in unleaded gasoline. It is manufactured by the catalytic conversion of acetylene to benzene: 3C₂H₂  C₆H₆

Draw Lewis structures for these compounds, with resonance structures as appropriate, and determine the hybridization of the carbon atoms in each.

Teflon is prepared by the polymerization of tetrafluoroethylene. Write the equation that describes the polymerization using Lewis symbols.

Write two complete, balanced equations for each of the following reactions, one using condensed formulas and one using Lewis structures.

(a) 2-butene reacts with chlorine.

(b) benzene burns in air.

What mass of 2-bromopropane could be prepared from 25.5 g of propene? Assume a 100% yield of product.

Ethylene can be produced by the pyrolysis of ethane: 

\[{{\rm{C}}_{\rm{2}}}{{\rm{H}}_{\rm{6}}}\to{{\rm{C}}_{\rm{2}}}{{\rm{H}}_{\rm{4}}}{\rm{+}}{{\rm{H}}_{\rm{2}}}\]

How many kilograms of ethylene is produced by the pyrolysis of 1.000 ×10³ kg of ethane, assuming a 100.0%yield?

Why do the compounds hexane, hexanol, and hexene have such similar names?

Write condensed formulas and provide IUPAC names for the following compounds: (a) ethyl alcohol (in beverages) (b) methyl alcohol (used as a solvent, for example, in shellac) (c) ethylene glycol (antifreeze) (d) isopropyl alcohol (used in rubbing alcohol) (e) glycerin

Give the complete IUPAC name for each of the following compounds

a)

b)

c)

Give the complete IUPAC name and the common name for each of the following compounds:

a)

b)

c)

Write the condensed structures of both isomers with the formula C₂H₆O. Label the functional group of each isomer.      

Write the condensed structures of all isomers with the formula C₂H₆O₂. Label the functional group (or groups) of each isomer.        

Draw the condensed formulas for each of the following compounds: (a) dipropyl ether (b) 2,2-dimethyl-3-hexanol (c) 2-ethoxybutane.          

MTBE, Methyl tert-butyl ether, CH₃OC(CH₃)₃, is used as an oxygen source in oxygenated gasolines. MTBE is manufactured by reacting 2-methylpropene with methanol. 

(a) Using Lewis structures, write the chemical equation representing the reaction.

(b) What volume of methanol, density 0.7915 g/mL, is required to produce exactly 1000 kg of MTBE, assuming a 100% yield? 

Write two complete balanced equations for each of the following reactions, one using condensed formulas and one using Lewis structures.

(a) propanol is converted to dipropyl ether

(b) propene is treated with water in dilute acid.

Write two complete balanced equations for each of the following reactions, one using condensed formulas and one using Lewis structures. (a) 2-butene is treated with water in dilute acid (b) ethanol is dehydrated to yield ethene

Order the following molecules from least to most oxidized, based on the marked carbon atom:

Predict the products of oxidizing the molecules shown in this problem. In each case, identify the product that will result from the minimal increase in oxidation state for the highlighted carbon atom:

a)

b)

c)

Predict the products of reducing the following molecules. In each case, identify the product that will result from the minimal decrease in oxidation state for the highlighted carbon atom:

Explain why it is not possible to prepare a ketone that contains only two carbon atoms.

How does the hybridization of the substituted carbon atom change when alcohol is converted into an aldehyde? An aldehyde to a carboxylic acid?

Fatty acids are carboxylic acids that have long hydrocarbon chains attached to a carboxylate group. How does a saturated fatty acid differ from an unsaturated fatty acid? How are they similar?

Write a condensed structural formula, such as\(C{H_3}C{H_3}\), and describe the molecular geometry at each carbon atom.

(a) 2-propanol

(b) acetone

(c) dimethyl ether

(d) acetic acid

(e) 3-methyl-1-hexene

Explain why it is not possible to prepare a ketone that contains only two carbon atoms. 

Write the two-resonance structures for the acetate ion.