Deck 7: Alkenes and Alkynes

Question 1

Instructions: Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate:

Answer 1

cis-3,3-dimethyl-4-propylocta-1,5-diene or (Z)-3,3-dimethyl-4-propylocta-1,5-diene

Question 2

Draw structures corresponding to each name below.

Draw:
trans-4,4-dimethylpent-2-ene

Answer 2

Question 3

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A)-COOH
B)-CHO
C)-CH₂OH
D)-CH₃

Answer 3

-COOH

Question 4

Calculate the degree of unsaturation in the formula below.Show your calculations.
caffeine,C₈H₁₀N₄O₂

Question 5

Instructions: Pent-2-ene is an example of a disubstituted alkene.Use this alkene to answer the following question(s).


Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.

Question 6

For a compound containing substituents other than hydrogen,the number of hydrogen atoms in the equivalent hydrocarbon formula is determined by _____ from the number of hydrogen atoms present.

A)subtracting the number of halogens atoms
B)adding two hydrogen atoms for each oxygen
C)subtracting the number nitrogen atoms
D)adding the number of oxygen atoms

Question 7

Instructions: Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate:

Question 8

Draw structures corresponding to each name below.
Draw:
(3E)-3,7-dimethylocta-1,3,6-triene

Question 9

The following group is a substituent on a molecule.What is an accepted IUPAC name for this group?

A)propenyl
B)allyl
C)vinyl
D)propylene
E)either a or b

Question 10

Match each definition to the term it describes.

Question 11

A molecule has three degrees of unsaturation.In this molecule there would be

A)three rings
B)three double bonds
C)two rings and one double bond
D)one ring and two double bonds
E)any of these

Question 12

Rank each set of substituents using the Cahn-Ingold-Prelog sequence rules by numbering the highest priority substituent 1 and numbering the lowest priority substituent 4.Place the number in the blank below the substituent.

Question 13

A compound with the following molecular formula contains two double bonds.What is the correct subscript for H in the formula?
C₁₀H_?ClN₂O

A)19
B)22
C)18
D)20
E)21

Question 14

Instructions: Dieldrin,C₁₂H₈Cl₆O,is a pentacyclic (five-ring)compound formerly used as an insecticide.Use this information to answer the following question(s).
Refer to instructions.Calculate the degree of unsaturation for Dieldrin.

Question 15

Instructions: Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate:

Question 16

Instructions: Pent-2-ene is an example of a disubstituted alkene.Use this alkene to answer the following question(s).

Refer to instructions.Circle the isomer of pent-2-ene that is most stable.

Question 17

Choose substituents X and Y (listed in order below)for the following compound so as to make a Z isomer.

A)-Br,-NHCH₃
B)-F,-CHO
C)-I,-OCH₃
D)-COOH,-CH₂NH₂
E)-Br,-COOH

Question 18

What is the IUPAC name of the following compound?

A)(E)-3-methylpent-3-ene
B)(Z)-3-methylpent-3-ene
C)(E)-3-methylpent-2-ene
D)(Z)-3-methylpent-2-ene

Question 19

Instructions: Dieldrin,C₁₂H₈Cl₆O,is a pentacyclic (five-ring)compound formerly used as an insecticide.Use this information to answer the following question(s).

Refer to instructions.How many double bonds does dieldrin have?

Question 20

Name this compound.

Question 21

Hydride shifts

A)occur to form less highly substituted carbocations.
B)occur by transfer of an H⁺ between adjacent carbon atoms.
C)are observed only in single step reactions.
D)transfer positive charge to a more highly substituted carbon atom.

Question 22

Predict the major organic product(s)in the reaction below.If more than one major organic product is expected,draw each one.Explain the significance of "35 ^$\circ$ C" and "ether" shown in the reaction.

Question 23

The following reaction is carried out in cyclohexane with the application of heat.Write the complete equation for the reaction below.If more than one major organic product is expected,draw each one.

Question 24

Below are all the chemical structures and intermediates involved in a reaction.On the structures provided,show all electron flow using the arrow formalism for the complete stepwise mechanism.

Question 25

Using curved arrows,write a mechanism for the following reaction.If carbocations are formed,specify if they are primary,secondary or tertiary.

Question 26

Which of the following would have the smallest DH ^$\circ$ _hydrog?

A)
B)
C)
D)

Question 27

Instructions: Assign E or Z configurations to each alkene below.
Assign:

Question 28

Below are all the chemical structures and intermediates involved in a reaction.Why does the rearrangement that results in the formation of product B occur?

Question 29

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A)-NH₂
B)-NHCH₃
C)-CH₂NH₂
D)-CH₂NHCH₃

Question 30

Rank the carbocations below in order of increasing stability (least stable = 1;most stable = 3).Place the number corresponding to the carbocation's relative stability in the blank below the structure.

Question 31

Alkene chemistry is dominated by what type of reaction?

A)substitution
B)electrophilic addition
C)nucleophilic addition
D)elimination
E)both b and c

Question 32

Predict the major organic product(s)in the reaction below.If more than one major organic product is expected,draw each one.

Question 33

What alkene would you use to prepare the following alkyl halide?

Question 34

Instructions: Assign E or Z configurations to each alkene below.
Assign: