Draw a structure for each compound (includes old and new names).

i. (3Z,6E)-1,3,6-octatriene

Label each structure as Z, E, or neither.

(a)

(b)

(c)

(d)

Determine which compounds show cis-trans isomerism. Draw and label the isomers, using both the cis-trans and E-Z nomenclatures where applicable.

a. pent-1-ene

b. pent-2-ene

Determine which compounds show cis-trans isomerism. Draw and label the isomers, using both the cis-trans and E-Z nomenclatures where applicable.

c. hex-3-ene

d. 1,1-dibromopropene

Give a correct name for each compound.

(a)

(b)

Give a correct name for each compound.

(c)

(d)

Give a correct name for each compound.

(e)

(f)

Draw and name all five isomers of formula C₃H₅F.

Draw all 12 acyclic (no rings) isomers of formula C₄H₇Br. Include stereoisomers.

Cholesterol, C₂₇H₄₆O, has only one pi bond. With no additional information, what else can you say about its structure?

Draw and name all stereoisomers of 3-chlorohepta-2,4-diene

a. using the cis-trans nomenclature.

Draw and name all stereoisomers of 3-chlorohepta-2,4-diene

b. using the E-Z nomenclature.

For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment.

a. cis-1,2-difluoroethene or trans-1,2-difluoroethene

For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment

b. cis-1,2-dibromoethene or trans-2,3-dibromobut-2-ene

For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment.

c. cis-1,2-dibromo-1,2-dichloroethene or cis-1,2-dichloroethene

The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the trans isomer of 4,4-dimethylpent-2-ene is nearly 16 kJ/mol more stable than the cis isomer. Explain this large difference.

A double bond in a six-membered ring is usually more stable in an endocyclic position than in an exocyclic position. Hydrogenation data on two pairs of compounds follow. One pair suggests that the energy difference between endocyclic and exocyclic double bonds is about 9 kJ/mol. The other pair suggests an energy difference of about 5 kJ/mol. Which number do you trust as being more representative of the actual energy difference? Explain your answer.

Predict the products of E1 elimination of the following compounds. Label the major products.

(a)

Predict the products of E1 elimination of the following compounds. Label the major products.

(c)

Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.

a. 1-bromobutane

b. 2-chlorobutane

c. 3-bromopentane

Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.

d. cis-1-bromo-2-methylcyclohexane

Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.

e. trans-1-bromo-2-methylcyclohexane

What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?

a. hex-1-ene

b. isobutylene

c. pent-2-ene

What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?

d. methylenecyclohexane

What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?

e. 4-methylcyclohexene

Predict the major products of acid-catalyzed dehydration of the following alcohols.

(a)

(b)

Predict the major products of acid-catalyzed dehydration of the following alcohols.

(c)

(d)

Predict the products of the following reactions. When more than one product is expected, predict which will be the major product.

Write a balanced equation for each reaction, showing the major product you expect.

(a)

Write a balanced equation for each reaction, showing the major product you expect.

(b)