Introduction to Organic Chemistry

Which of the following is a false statement about organic chemistry?

Which of the following is true about carbon?

Alkanes have a general formula of

(a) What is the difference between chlorofluorocarbons and hydrofluorocarbons?

Cyclopropane is an interesting hydrocarbon. Instead of having three carbons in a row, the three carbons form a ring, as shown in this perspective drawing (see Figure 2.18 for a prior example of this kind of drawing):

Cyclopropane was at one time used as an anesthetic, but its use was discontinued, in part because it is highly flammable. (a) How does it differ from that of propane?

Butane and methylpropane are examples of _________.

The type of isomerism in alkenes that is due to restricted rotation is

Write structural formulas for each of the nine structural isomers of heptane.

Determine whether the molecules in each pair are the same or enantiomers. c.

Determine whether the molecules in each pair are the same or enantiomers. c.

Methionine, one of the 20 amino acid building blocks from which proteins are made, has the following structure. What is the chemical formula of methionine? In writing the for-mula, list the element symbols in alphabetical order, and give the number of each element as a subscript.

Dichloroethylene 1C2H2Cl22 has three forms (isomers), each of which is a different substance. (c) How many isomeric forms can chloroethylene, C2H3Cl, have? Would they be expected to have dipole moments?

Dichloroethylene 1C2H2Cl22 has three forms (isomers), each of which is a different substance. (a) Draw Lewis structures of the three isomers, all of which have a carbon–carbon double bond.

Write structural formulas for each of the possible isomers of n-pentyne that are formed by moving the position of the triple bond.

(b) Among the four alkanes, ethane, propane, butane, and pentane, which is capable of existing in isomeric forms?

Chloropropane is derived from propane by substituting Cl for H on one of the carbon atoms. (a) Draw the structural formulas for the two isomers of chloropropane.

Determine whether the two structures are isomers or the same molecule drawn in two different ways. b.

Determine whether the two structures are isomers or the same molecule drawn in two different ways. c.

Draw the structure that corresponds to each name and indicate which structures can exist as stereoisomers. b. 3,5-dimethyl-2-hexene

Identify the two compounds that display stereoisomerism and draw their structures. e. 2,4-dimethyl-3-pentanol

Cyclopropane is an interesting hydrocarbon. Instead of having three carbons in a row, the three carbons form a ring, as shown in this perspective drawing (see Figure 2.18 for a prior example of this kind of drawing):

Cyclopropane was at one time used as an anesthetic, but its use was discontinued, in part because it is highly flammable. (b) The three carbon atoms are necessarily in a plane. What do the different wedges mean?

Section 2.9 introduced the idea of structural isomerism, with 1-propanol and 2-propanol as examples. Determine which of these properties would distinguish these two substances: (a) boiling point, (b) combustion analysis results, (c) molecular weight, (d) density at a given temperature and pressure. You can check on the properties of these two compounds in Wolfram Alpha (http://www.wolframalpha.com/) or the CRC Handbook of Chemistry and Physics.

Write the structural formulas of three different compounds that each have the molecular formula C5H12.

Cyclohexane, C6H12, is an important starting material used in the industrial synthesis of nylon. Each carbon has four covalent bonds, two to hydrogen and two to other carbons. Draw the structural formula of cyclohexane.

Isooctane, the substance in gasoline from which the term octane rating derives, has the formula C8H18. Each carbon has four covalent bonds, and the atoms are connected in the sequence shown. Draw the complete structural formula of isooctane.

Fructose, C6H12O6, is the sweetest naturally occurring sugar and is found in many fruits and berries. Each carbon has four covalent bonds, each oxygen has two covalent bonds, each hydrogen has one covalent bond, and the atoms are connected in the sequence shown. Draw the complete struc-tural formula of fructose.

Chiral compounds

Determine whether each compound exhibits optical isomerism c.

Determine whether each compound exhibits optical isomerism c.

(a) What is meant by the term isomer?

The correct IUPAC name for an organic compound is 4-ethyl-3,6-dimethyldecane. This compound is:

Based on the molecular formula, determine whether each com- pound is an alkane, alkene, or alkyne. (Assume that the hydro- carbons are noncyclical and there is no more than one multiple bond.) a. C5H12 b. C3H6 c. C7H12 d. C11H22

Name each alkane. d.

Name each alkane. c.

Draw a structure for each alkane. d. 4,7-diethyl-2,2-dimethylnonane

Draw a structure for each alkane. c. 4-ethyl-2,2-dimethylhexane

(a) Draw Lewis structures for chloromethane 1CH3Cl2, chloroethene 1C2H3Cl2, and chloroethyne 1C2HCl2. Draw Lewis structures for chloromethane 1CH3Cl2.

Name each compound. a.

Name each alkene. c.

Name each alkene. c.

Draw the correct structure for each compound. d. 5-ethyl-3,6-dimethyl-2-heptene

Draw the correct structure for each compound. d. 3-ethyl-4-methyl-2-pentene

(a) Draw Lewis structures for chloromethane 1CH3Cl2, chloroethene 1C2H3Cl2, and chloroethyne 1C2HCl2. Draw Lewis structures for chloroethene 1C2H3Cl2.

Name each compound. a.

Name each alkyne. d.

Name each alkyne. d.

Draw the correct structure for each compound. c. 3,3-dimethyl-1-pentyne

(a) Draw Lewis structures for chloromethane 1CH3Cl2, chloroethene 1C2H3Cl2, and chloroethyne 1C2HCl2. Draw Lewis structures for chloroethyne 1C2HCl2.

Name each monosubstituted benzene. b.

Name each monosubstituted benzene. c.

Name each compound in which the benzene ring is best treated as a substituent. b.

Name each compound in which the benzene ring is best treated as a substituent. . c.

Name each disubstituted benzene. c.

Name each disubstituted benzene. b.

Draw the structure for each compound. b. meta-dibromobenzene

Draw the structure for each compound. a. ethylbenzene

Draw the structure for each compound. b. 1-iodo-2-methylbenzene

Name each alcohol. c.

Name each alcohol. a.

Draw the structure for each alcohol. c. 3-ethyl-1-hexanol

Name each aldehyde or ketone. d.

Name each aldehyde or ketone. c.

Draw the structure of each aldehyde or ketone. c. 2-methylbutanal

Name each carboxylic acid or ester.

Name each carboxylic acid or ester.

Draw the structure of each carboxylic acid or ester. c. 3-ethylheptanoic acid

Draw the structure of each carboxylic acid or ester. b. methyl hexanoate

(b) Pentane is the alkane with a chain of five carbon atoms. Determine its molecular formula.

Name each ether. b.

Draw the structure for each ether. c. methyl hexyl ether

Name each amine b.

Chloropropane is derived from propane by substituting Cl for H on one of the carbon atoms. (b) Suggest names for these two compounds.

Draw the structure for each amine. c. butylethylamine

Name each compound. c.

Name each compound. b.

Name each compound. d.

Name each compound. b.

Name each compound. c.

In the presence of heat or light, chloromethane gas will react with a stoichiometric amount of chlorine gas to produce which of the following products?

CH₃Cl (g) + Cl₂ (g) →

Alcohol-based fuels for automobiles lead to the production of formaldehyde (CH2O) in exhaust gases. Formaldehyde undergoes photodissociation, which contributes to photo- chemical smog: CH2O + hn ¡ CHO + H The maximum wavelength of light that can cause this reac- tion is 335 nm. (d) Write out the formaldehyde photodis- sociation reaction, showing Lewis-dot structures.

List all the possible products for each alkane substitution reac- tion. (Assume monosubstitution.) d.

List all the possible products for each alkane substitution reac- tion. (Assume monosubstitution.) a. CH3CH3 + Br2 ¡

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.) d. CH3CHBr2 + Br2 ¡

What is the organic product when 1-pentene reacts with hydrogen bromide?

List the products of each alkene addition reaction. c.

What are the products of each alkene addition reaction? d.

What are the products of each alkene addition reaction? a.

Complete each hydrogenation reaction. c.

Complete each hydrogenation reaction. b.

Determine the product of the addition reaction.

Determine the products of each reaction. a.

The hydrogen at C-1 of 1-butyne is much more acidic than the one at C-1 in 1-butene. Explain.

The prefix meta- refers to

Which of the following does not characterize aromatic compounds?

What are the products of each aromatic substitution reaction? a.

What are the products of each aromatic substitution reaction? b.

The following molecule contains which functional group?

CH₃– CH₂– CH₂– CH₂– CH–COOH

Teflon is an addition polymer formed from the monomer shown here. Draw the structure of the polymer.

Saran, the polymer used to make saran wrap, is an addition polymer formed from two monomers—vinylidene chloride and vinyl chloride. Draw the structure of the polymer. (Hint: The monomers alternate.)

Polyacrylonitrile (PAN) is an addition polymer with the struc- ture shown here. Draw the structure of the monomer.

(b) Which of these molecules can be used as a monomer: ethanol, ethene (also called ethylene), methane?

(c) Write a structural formula for 1-pentanol, the alcohol derived from pentane by making a substitution on one of the carbon atoms.

Consider the following organic substances: ethylethanoate, ethylmethylether, hexanol, and propanone. (b) Which of these molecules contain a C = O group?

Consider the following organic substances: ethylethanoate, ethylmethylether, hexanol, and propanone. (a) Which of these molecules contains three carbons?

Write a balanced chemical equation for the formation of a polymer via a condensation reaction from the monomers succinic acid 1HOOCCH2CH2COOH2 and ethylenediamine 1H2NCH2CH2NH22.

Write the chemical equation that represents the formation of (b) polyacrylonitrile from acrylonitrile (polyacrylonitrile is used in home furnishings, craft yarns, clothing, and many other items).

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound. e.

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound. c.

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound. a.

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound. d.

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound. a.

What molecular structural features cause high-density polyethylene to be denser than low-density polyethylene?

There are eight structures with the formula C3H7NO in which the O is part of a carbonyl group. Draw the structures and identify the functional groups in each.

Employing the bond enthalpy values listed in Table 8.4, estimate the molar enthalpy change occurring upon (c) formation of polyethylene terephthalate (PET).

Small molecules with C“C double bonds, called monomers, can join with one another to form long chain molecules called polymers. Thus, acrylonitrile, H2C“CHCN, polymerizes under appropriate conditions to give polyacrylonitrile, a common starting material for producing the carbon fibers used in composites. (b) Use the bond dissociation energies in Table 7.1 to calculate ΔH per H2C“CHCN unit for the conversion of acrylonitrile to polyacrylonitrile. Is the reaction endothermic or exothermic?

Small molecules with C“C double bonds, called monomers, can join with one another to form long chain molecules called polymers. Thus, acrylonitrile, H2C“CHCN, polymerizes under appropriate conditions to give polyacrylonitrile, a common starting material for producing the carbon fibers used in composites. (a) Write electron-dot structures for acrylonitrile and polyacrylonitrile, and show how rearranging the electrons can lead to formation of the polymer.

A carboxylic could be formed by the ____________ of alcohols.