Test 2 Ch.8-10

An acyclic hydrocarbon has a molecular formula C21H42. Which class of compounds does it

belong to?

alkene

An unsaturated compound with one triple bond and no double bonds has a molecular formula

C10H16. How many rings does the molecule have?

a) 0

b) 1

c) 2

d) 3

b

Exercise 3. A compound C5H7Br has:

a) Two double bonds

b) Two double bonds and a ring

c) Two triple bonds

d) Two double bonds and a triple bond

a

Draw the formulas of vinylcyclohexane and allylcyclopentane.

a

1-ethylcyclopentene; 3-propyl-2-hexene; (E)-2-pentene; 3-vinylcyclopentene; 1-allylcyclopentene; 3-propyl-1-heptene

trans arrangement has dipoles that largely cancel, cis creates a small dipole-dipole interaction, the triple bond makes it difficult to break

Draw all the isomeric compounds with the formula C4H8:

a

Draw.

a

Convert the multiple bonds in the following two substituents into single bonds by adding virtual

atoms. Which of the two substituents has the higher priority? What is the Cahn-Ingold-Prelog designation of

the stereochemistry of the double bond?

the top; E

Estimate bond angles in the following molecule. draw and type a

a

Provide formulas of ethynylcyclohexane and propargylcyclopentane.

a

A hydrocarbon with ten carbons has three degrees of unsaturation. What is its molecular formula?

C10H16

What hybrid orbitals are used to make bonds between the atoms given in bold?

sp-sp2; sp2-sp3

Draw a complete structural formula of CH3CH2CH2C(=CH2)CH(CH3)2. Name this alkene.

2-isopropyl-1-pentene

A ring that contains eight, or more, carbon atoms can accommodate a triple bond. The naming of such cyclic compounds is analogous to the naming of cycloalkenes. One should use a prefix cyclo and a suffix yne. Name the following compound.

6-ethylcyclodecyne

Name this compound

(Z)-3,4-dimethyl-3-heptene

Name this compound

(E)-2-pentene

Name this compound

2,3-dimethyl-2-hexene

Name this compound

2-ethyl-1-hexene

Name this compound

1-bromo-2,3-dimethyl-2-butene

Name this compound

6,6-dimethyl-3-propyl-1-heptene

Draw this compound: 4,4-dibromo-1-pentene

a

Draw this compound: 1-methylcyclopentene

a

Draw this compound: 3-bromocyclobutene

a

Draw this compound: 3-iodo-1-butyne

a

Draw this compound: (Z)-4-bromo-2-pentene

a

An unsaturated compound with one double bond and no triple bonds has a molecular formula C8H14.

How many rings does the molecule have?

a) 0

b) 1

c) 2

d) 3

b

c

d

a

Which of the following is the best description of a carbon-carbon double bond?

a) A double bond is made by side to side overlap of atomic p orbitals.

b) A double bond is composed of a sigma and a pi orbital.

c) A double bond consists of two bonds of equal strength.

d) Carbon atoms of the double bonds have bent geometry.

b

An unsaturated compound with one ring and no triple bonds has a molecular formula C9H14. How many

double bonds does the molecule have?

a) 1

b) 2

c) 3

d) 4

b

A hydrocarbon with twelve carbon atoms has two rings and a double bond. How many hydrogen atoms

does the molecule have?

a) 12

b) 18

c) 20

d) 24

c

Name this compound

1-hepten-6-yne

Name this compound

(2E,4E)-2,4-hexadiene

Name this compound

3-propyl-1,6-heptadiene

Name this compound

1-methyl-1,3-cyclohexadiene

Name this compound

3-bromo-1-hepten-6-yne

Name this compound

5-methyl-2,5-cycloheptadienol

Name this compound

(E)-2-heptene

Draw this compound: 3-methylcyclopentene

a

Name this compound

(Z)-2-hexene

Draw this compound: 3,3-dimethylcyclopentene

a

Name this compound

(Z)-3,4-dimethyl-3-heptene

Draw this compound: 4-bromo-2-pentyne

a

Name this compound

2-ethyl-5,5-dimethyl-1-hexene

Draw this compound: 1-bromo-1-pentyne

a

Name this compound

(E)-6,6-dimethyl-3-heptene

III,I,II,IV

Draw.

a

draw.

a

D,A,C,B

A compound with a molecular formula C10H14 reacts with two equivalents of bromine. How

many rings does the molecule have?

2

As stated above, the carboxylic group usually does not interfere with the addition of bromine

unless it is in the vicinity of the double bond as in the case of 4-pentenoic acid. What do you think is the

reaction product? draw

a

How would you make 2-bromo-1-chloropropane? Draw and type a

a

What is this?

Acetyle or Ac

What is this?

Acetate or OAc

Draw

a

draw

a

c

Name this compound

peracetic acid

Name this compound and its abreviation

m-chloroperbenzoic acid (m-CPBA)

Name this compound

trifluoroperacetic acid

draw

a

draw

a

draw

a

c,d,a,b