Work sheet organic chemistry

(Use the following information for questions 10-11.) Again, considering the polar reaction we
used in class for an example of reaction mechanisms and the following reaction profile:

10. Which point(s) represent transition state(s)?

a) 2 only (b) 3 only (c) 4 only (d) 2 and 4 (e) 2, 3, and 4

11. Which point(s) represent an intermediate?

a) 2 only (b) 3 only (c) 4 only (d) 2 and 4 (e) 2, 3, and 4

12. All of the following statements are true about SN2 reaction except

(a) It is a one-step process (b) It is bimolecular process (c) It is second order kinetics

(d) Branching at the reacting carbon increases the rate of reaction (e) none

13. Which ion is the strongest nucleophile in aqueous solutions?

a) F- (b) Cl- (c) Br- (d) I- (e) all of these are equally strong

14. Which of the following is the BEST leaving group for SN2 reactions?

a) I- (b) F- (c) Cl- (d) Br-

15. Identify the nucleophile in the following reaction:

RX + H2O  ROH + HX

a) X- (b) H+ (c) H2O (d) ROH (e) RX

16. The SN2 reaction mechanism best applies to

(a) cyclopropane and H2 (b) 1-chlorobutane and aq. NaOH (c) KOH and NaOH

(d) ethane and H2O (e) None

1
17. Which of the following haloalkanes will undergo hydrolysis more rapidly?

(a) (CH3)3CF (b) (CH3)3CCl (c) (CH3)3CBr (d) (CH3)3CI (e) None

For Questions 18-19 refer the following reaction equation

18. The above reaction is second order. Given the rate constant K= 3.5x 10-3 L mol-1 s-1. What is the
observed rate at the following concentrations? [CH3Cl] = 0.50 mol L-1 ; [OH] = 0.015 mol L-1

(a) 2.6 x10-5 mol L-1 s-1 (b) 2.6 x 10-6 mol L-1 s-1 (c) 2.6 x10-3 mol L-1 s-1 (d) 1.75 x10-5 mol L-1 s-1

(e) 1.75 x10-3 mol L-1 s-1

19. How would the rate of the above reaction be affected by replacing OH- with C2H5O- ?

(a) increases (b) decreases (c) remains constant (d) none

20. The reaction (CH3)3CCl + CH3O-  (CH3)2C=CH2 is an example of which of the following
processes?

(a) E1 (b) E2 (c) SN1 (d) SN2 (e) None

21. Which reaction intermediate is believed to be part of the reaction shown?

(a) radical (b) carbocation (c) oxacyclopropane (d) bromonium ion (e) None

22. A chiral compound, C5H8, upon simple catalytic hydrogenation yields an achiral compound,

C5H10. What is the structure of the former?

23. When 1-pentene is treated with peroxides free HBr, which of the following compounds is the
resulting product?

(a) 1-bromopentene (b) 1-pentyne (c) pentane (d) 2-bromopentane (e) 2-bromobutane

Part II Give your answer on the space provided.

1. Write the product of each of the following bimolecular substitution. (1 pt. each)

2
 2. What is the major substitution product of each of the following solvolysis reactions? ( 2 pts each)

3. The following reaction can proceed both by E1 & E2 mechanisms.

The E1 rate constant is KE1=1.4x10-4s-1 and the E2 rate constant KE2=1.9x10-4Lmol-1s-1,

0.02M haloalkane.

a) What is the predominant elimination mechanism with 0.5M NaOCH 3? (2 pts.)_____________

b) What is the predominant elimination mechanism with 2.0M NaOCH 3? (2 pts.)______________

c) At what concentration of the base does exactly 50% of the starting material react by an E1 route
and 50% by E2 path way? (2 pts.)________________________

4. Explain the fact that whereas 2-Bromopentane undergoes dehydrohalogenation with C 2H5O-K+ to
give mainly 2-pentene (Saytzeff product), with Me3CO-K+ it gives mainly 1-pentene the anti-
Saytzeff , Hofmann product. (2 Pts)

I. Give the expected major product of the following reaction, no reaction mechanism is required (2
pts each)

(b) acetaldehyde + hydrazine 

3
 II. Rewrite each of the following reactions using chemical equations (no reaction mechanism is required)
(2 pts each)

a) Preparation of 2-butanol using appropriate Grignard reagent and propanal and subsequent
hydrolysis
b) Crossed aldol reactionof propanal with benzaldehyde
c) Claisen condensation of ethyl acetate
d) Crossed Cannizzaro reaction of formaldehyde with benzaldehyde

I. Circle the letter that corresponds to the correct answer. (1 mark each)

1. The intermediate cation A in the sequence

2. Which of the following isomeric carbocations is the more stable ?

4
3. Among the following choices, the group that activates the benzene ring toward electrophilic aromatic
substitution is

(a) -NO2 (b) -CF3 (c) -COOH (d) -OH (e) -Br (f) none

4. Among the following choices, the group that deactivates the benzene ring toward

electrophilic aromatic substitution is

(a) -OH (b) -CH3 (c) -COOH (d) -OCH3 (e) -NH2 (f) none

5. A student in lab class runs a nitration reaction using two substrates. The first is chlorobenzene and the
second is toluene. Which of the following statements is TRUE?

(a) The reactions proceed at the same rate.

(b) The reaction with chlorobenzene proceeds more rapidly.

(c) The reaction with toluene proceeds more rapidly.
(d) It is not possible to differentiate between the two in terms of rate
6. Geminal diols are formed by the reaction of ______ with water.

(a) aldehydes (b) ketones (c) alcohols (d) a & b (e) all

7. Which one of the following is a carbon nucleophile?

(a) HCl (b) RLi (c) C2H5OH (d) NH3 (e) none

8. The structure PhCH(OC2H5)2 represents an acetal derived from ethanol and _____.

(a) phenol (b) benzene (c) benzaldehyde (d) acetophenone (e) none

9. One of the following is NOT a nitrogen nucleophile?

(a) Hydrazine (b) hydroxylamine (c) urea (d) 2,4-DNPH (e) none

10. Reaction of an unknown aldehyde with the Girignard reagent and subsequent acidic

hydrolysis gives 2- butanol. What was the unknown aldehyde?

(a ) ethanal (b) methanal (c) propanal (d) butanal

5
11. How many α-Hydrogens are there in 3-methyl-1-phenyl-2-butanone?

(a) 1 (b) 2 (c) 3 (d) 4 (e) 0

12. How many α-Hydrogens are there in 2-propanone?

(a) 6 (b) 8 (c) 3 (d) 4 (e) 0

13. Which one of the following is a haloform?

(a) HI (b) H2CI2 (c) HCI3 (d) H3CI

II. Complete the following reaction ( no reaction mechanism is required) (2 pts

each)

6
III. Give your answers on the space provided (no reaction mechanism is
required) (2 marks)

1. Give the structure of the enolate ion arising from deprotonation of

cyclohexanone

2. Write the product of the base-catalyzed bromination of cyclohexanone.

3. Can 2,2-dimethylpropanal undergo Aldol condensation with itself? Yes or No

4. Rewrite the Cannizzaro reaction of Formaldehyde with Benzaldehyde.

5. Rewrite the Claisen condensation of ethyl acetate.