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Name:

Orgo1-Test 2

Short Answer

Class:

Date:

Draw structures corresponding to each of the following names.

1.

2.

3.

cis-1-sec-butyl-2-ethylcyclopentane

3,5-dicyclohexylnonane

Draw the two stereoisomers of 1,3-dibromocyclobutane.

For the pair of molecules below, circle the more stable one.

4.

CH 3

CH 3

H H
H
H

CH 3

H
H

H

H H

CH 3

and

CH 3

CH 3

Classify each reaction below as a(n):

a. addition

b. elimination

c. substitution

d. rearrangement

ID: A

Place the letter corresponding to the correct answer in the blank to the left of the reaction.

5.

6.

7.

ID: A Place the letter corresponding to the correct answer in the blank to the left
ID: A Place the letter corresponding to the correct answer in the blank to the left
ID: A Place the letter corresponding to the correct answer in the blank to the left

1

Name:

ID: A

Identify the functional groups present in the compound below and predict the direction of polarity in each.

8.

mustard gas Cl CH 2 CH 2 S CH 2 CH 2 Cl

9.

9.

Classify each structure below as a nucleophile or electrophile and briefly explain your choice.

10.

10.

11.

11.

12.

12.

Identify the nuclephile and electrophile in each reaction below and label them.

13.

13.

14.

14.

2

Name:

ID: A

Consider this reaction when answering the following question(s):

this reaction when answering the following question(s): 15. This reaction is an example of: a. a

15. This reaction is an example of:

a. a substitution reaction.

b. a rearrangement reaction.

c. an addition reaction.

d. an elimination reaction.

Use the reaction energy diagram below to answer the following question(s).

energy diagram below to answer the following question(s). 16. The reaction depicted in this reaction energy

16. The reaction depicted in this reaction energy diagram can best be described as:

a. a slow exothermic reaction

b. a fast exothermic reaction

c. a slow endothermic reaction

d. a fast endothermic reaction

17. The transition state is found at point

18. The products are found at point

19. The free-energy change for the reaction is indicated at point

20. The reactants are found at point

on the diagram.

on the diagram.

on the diagram.

3

on the diagram.

Name:

ID: A

Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following question(s).

water, shown below, to answer the following question(s). Diagram 1 : The first step of this

Diagram 1: The first step of this reaction is shown below.

Diagram 1 : The first step of this reaction is shown below. Diagram 2 : The

Diagram 2: The second and third steps of the reaction are shown below.

The second and third steps of the reaction are shown below. 21. Using the bond dissociations

21. Using the bond dissociations values in the table below, calculate the Hfor the reaction in Diagram 2 above. Show your calculations for full credit.

Bond

D (kJ/mol)

(CH 3 ) 3 C Br

263

(CH 3 ) 3 C OH

380

HO H

498

H Br

366

Calculate the degree of unsaturation in each formula below. Show your calculations.

22. pinene, C 10 H 18

23. diazepam (Valium), C 16 H 13 N 2 OCl

Draw structures corresponding to each name below. Either condensed or line structures may be used.

24. 3,6-dimethyl-1,4-cyclohexadiene

4

Name:

ID: A

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

25.

Name:

25. Name: Rank each set of substituents using the Cahn-Ingold-Prelog sequence rules by numbering the highest

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.

26.

26.

Assign E or Z configurations to each alkene below.

27.

27.

28.

28.

Predict the major organic product for each reaction below.

29.

29.

5

Name:

30.

Name: 30. 6 ID: A

6

ID: A

Orgo1-Test 2 Answer Section

SHORT ANSWER

1.

ANS:

 
 

CH 3

 

CH 2 CH 3

 

CHCH 2 CH 3

 
H
H

H

 

PTS:

1

2.

ANS:

2 CH 3   H H   PTS: 1 2. ANS: PTS: 1 3. ANS:  

PTS:

1

3.

ANS:

 

Br

Br

 

Br

and Br

and

and Br

Br

 

cis

trans

 

PTS:

1

4.

ANS:

CH 3 H H H CH 3 CH 3
CH 3
H
H
H
CH 3
CH 3

and

PTS:

1

5.

ANS:

c

PTS:

1

 
CH 3 H CH 3 H CH 3
CH 3
H
CH 3
H
CH 3

H

1

ID: A

ID: A

6.

ANS:

d

PTS:

1

7.

ANS:

a

PTS:

1

8.

ANS:

6. ANS: d PTS: 1 7. ANS: a PTS: 1 8. ANS: PTS: 1 9. ANS:

PTS:

1

9.

ANS:

1 7. ANS: a PTS: 1 8. ANS: PTS: 1 9. ANS: PTS: 1 10. ANS:

PTS: 1

10.

ANS:

Azide is a nucleophile since it has a net negative charge (and lots of electron pairs!).

PTS: 1

11.

ANS:

Hydronium ion is an electrophile since it has a positive charge.

PTS: 1

12.

ANS:

Phenol can be a nucleophile or an electrophile

since it has a positive charge. PTS: 1 12. ANS: Phenol can be a nucleophile or

PTS:

1

2

ID: A

13.

ANS:

13. ANS: PTS: 1 14. ANS: PTS: 1 15. ANS: b PTS: 1 16. ANS: b

PTS:

1

14.

ANS:

13. ANS: PTS: 1 14. ANS: PTS: 1 15. ANS: b PTS: 1 16. ANS: b

PTS:

1

15.

ANS:

b

PTS:

1

16.

ANS:

b

PTS:

1

17.

ANS:

B

PTS:

1

18.

ANS:

D

PTS:

1

19.

ANS:

C

PTS:

1

20.

ANS:

A

PTS:

1

3

21. ANS:

H

= Hbonds broken Hbonds formed

= 761 kJ/mol 746 kJ/mol

= +15 kJ/mol

Bonds Broken

Bonds Formed

ID: A

(CH 3 ) 3 C Br

263 kJ/mol

(CH 3 ) 3 C OH

380 kJ/mol

HO H

498 kJ/mol

H Br

366 kJ/mol

761 kJ/mol

746 kJ/mol

PTS: 1

22. ANS:

The saturated ten carbon compound would have 22 hydrogens so the number of degrees of unsaturation is:

(22

18) 2 = 4 2 = 2.

PTS: 1

23. ANS:

Oxygen does not affect the base formula. A hydrogen is added to the base formula for each halogen and subtracted for each nitrogen so the base formula for diazepam is C 16 H 12 . The saturated 16 carbon compound would have 34 hydrogens so the number of degrees of unsaturation for diazepam is: (34 12) 2 = 22 2 =

11.

PTS:

1

24. ANS:

is: (34 12) ∏ 2 = 22 ∏ 2 = 11. PTS: 1 24. ANS: PTS:

PTS:

1

25. ANS:

(2E,4E)-5-ethyl-6-methyl-2,4-heptadiene

PTS:

1

26. ANS:

11. PTS: 1 24. ANS: PTS: 1 25. ANS: (2 E ,4 E )-5-ethyl-6-methyl-2,4-heptadiene PTS: 1

27.

PTS:

ANS:

E

PTS:

1

1

4

28. ANS:

E

PTS:

1

29. ANS:

28. ANS: E PTS: 1 29. ANS: PTS: 1 30. ANS: PTS: 1 5 ID: A

PTS:

1

30. ANS:

28. ANS: E PTS: 1 29. ANS: PTS: 1 30. ANS: PTS: 1 5 ID: A

PTS:

1

5

ID: A