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Exam 2 on Introduction to Organic Chemistry | CHM 122, Exams of Organic Chemistry

Material Type: Exam; Class: Introduction to Organic Chemistry; Subject: Chemistry; University: Wake Forest University; Term: Spring 2002;

Typology: Exams

Pre 2010

Uploaded on 08/19/2009

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Exam 2 Chm 122 Spring ‘03
1. (2 points) Circle the strongest acid.
CH3OH BrCH2OH Br2CHOH
2. (4 points) Circle the strongest base in each set.
a) CH3CH3CH3OLi CH3NHNa
b) CH3CH2OH CH3CH2ONa
O
C ONaCH3
3. (6 points) The following alcohols may look similar on paper, but they behave quite
differently in acid/base reactions. One has a pKa of 10 and the other has a pKa of 16. Which
compound has which pKa? In the space provided explain your reasoning.
OH OH
Exam 2 Chm122 Summer ‘02
4. (6 points) Rank the following compounds in order of increasing acidity. Clearly indicate
which is most acidic in each set.
a)
CH
3
CHOH
Br
CH
3
CH
2
OH BrCH
2
CH
2
OH
b)
(CH
3
)
2
NH
2
(CH
3
)
2
NH CH
3
OH
5. (6 points) Rank the following compounds in order of increasing basicity. Clearly indicate
which is most basic in each set.
a)
HC CNa H
2
C CHNa CH
3
CH
2
Na
b)
CH
3
NH
2
CH
3
OH CH
3
SH
pf3
pf4
pf5

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Exam 2 Chm 122 Spring ‘

1. (2 points) Circle the strongest acid.

CH 3 OH BrCH 2 OH Br 2 CHOH

2. (4 points) Circle the strongest base in each set.

a) CH 3 CH 3 CH 3 OLi CH 3 NHNa

b) CH 3 CH 2 OH CH 3 CH 2 ONa

O

CH 3 C ONa

3. (6 points) The following alcohols may look similar on paper, but they behave quite

differently in acid/base reactions. One has a pKa of 10 and the other has a pKa of 16. Which

compound has which pKa? In the space provided explain your reasoning.

OH OH

Exam 2 Chm122 Summer ‘

4. (6 points) Rank the following compounds in order of increasing acidity. Clearly indicate

which is most acidic in each set.

a) CH^3 CHOH

Br CH 3 CH 2 OH BrCH 2 CH 2 OH

b) (CH^3 )^2 NH^2 (CH^3 )^2 NH^ CH^3 OH

5. (6 points) Rank the following compounds in order of increasing basicity. Clearly indicate

which is most basic in each set.

a) HC^ CNa^ H^2 C^ CHNa^ CH^3 CH^2 Na

b) CH^3 NH^2 CH^3 OH^ CH^3 SH

Exam 1 Chm221 Fall ‘

6. (6 points) Circle the strongest acid in each of the two sets.

a) CH 3 OH CH 3 NH 2 CH 3 SH CH 4

b) CH 3 CH 2 CO 2 H CH 3 CHClCO 2 H CH 3 CCl 2 CO 2 HCHCl 2 CH 2 CO 2 H

7. (3 points) Circle the strongest base.

CH 3 O-^ CH 3 CH 2 O-^ (CH 3 ) 2 CHO-^ (CH3)3CO-

8. (3 points) Rank the following compounds in order of increasing acidity. Clearly indicate

which is most acidic.

H 2 S H 3 O+^ H 3 N

9. (3 points) Rank the following compounds in order of increasing basicity. Clearly indicate

which is most basic.

CH 3 Li H 3 N (CH 3 ) 3 COK

Exam 1 Chm221 Fall ‘

10. (3 points) Rank the following compounds in order of increasing acidity. Clearly indicate

which is most acidic.

CH 3 CHBrCOH

O

BrCH 2 CH 2 COH

O

CH 3 CBr 2 COH

O

11. (3 points) Rank the following compounds in order of increasing basicity. Clearly indicate

which is most basic.

CH 3 NH CH 3 CH 2 OH CH 3 CH 3

Exam 1 Chm221 Summer ‘

12. The following compound can be protonated at any one of the three nitrogen atoms. One of

the nitrogens is much more basic than the other two. Draw products of the protonation of

each of the three nitrogens (3 reactions). Draw any important resonance structures for the 3

products you obtain. Using the resonance structures, determine which N is most basic. (

points)

CH 3 CH 2 COH

O

  • CH 3 CH 2 ONa CH 3 NH 2 + H 2 SO 4

Exam 1 Chm221 Fall ‘

CH 3 CH 2 CH 2 CH 2 Li (^) + HC CCH 2 CH 3 O C CH 3 CH 2 ONa

+ CH 3 OH

H 2 SO 4 + CH 3 CH 2 NHCH 3

Final Exam Chm221 Fall ‘

CH 2 CH 2 CH 2 COH

Cl

O

  • CH 3 CH 2 CHCONa

O

Cl O C (CH 3 ) 3 C NH 2

  • (CH 3 ) 2 NLi CH 3 OH (^) + CH 3 SNa

Exam 1 Chm221 Summer ‘

CH 3 Li (^) + CH 3 OH

(fill in missing reagents)

(CH 3 ) 3 COH + + H 2

CH 3 CH 2 SNa (^) + + NaNH 2

Final Exam Chm221 Summer ‘

OH

O

Cl ONa

O

Br

ONa

O

+ OH

CH 3 CH 2 CH 2 CH 2 Li (^) + CH 3 CH 2 C CH

Exam 1 Chm221 Fall ‘

CH 3 S

+ (CH 3 ) 2 NH

O

C

H OH

+ CH 3 CH 2 OK

H 2 SO 4 +

CH 3 CNH 2

O

Final Exam Chm221 Fall ‘

CH 3 CH 2 CONa

O

+ CH 3 CH 2 OH

(CH 3 CH 2 ) 2 NH 2 Cl^ + NaOH CF 3 COH

O

CCl 3 CONa

O

Exam 1 Chm221 Summer ‘

O

CH 3 C OH

O

CHBr 2 C O (CH 3 ) 2 CH C C H + LiCH 3 (CH 3 ) 3 N (^) + HI CH 3 S K (^) + H 2 O