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40 Questions on Exam 4 for Organic Chemistry I | CHM 2210, Exams of Chemistry

Material Type: Exam; Professor: Keller; Class: Organc Chem I; Subject: Chemistry; University: Florida International University; Term: Fall 2011;

Typology: Exams

2011/2012

Uploaded on 09/09/2012

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Last Name, First Name__________________________ Panther ID_____________
FLORIDA INTERNATIONAL UNIVERSITY
Department of Chemistry & Biochemistry
CHM 2210-U01 – ORGANIC CHEMISTRY I
Fall 2011
EXAM IV
Dr. Keller/Dr. Landrum
Version 2
Instructions: Choose the BEST answer to each multiple choice question.
Look over the Written Questions early during your test to be sure you allocate your time appropriately.
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Last Name, First Name__________________________ Panther ID_____________

FLORIDA INTERNATIONAL UNIVERSITY

Department of Chemistry & Biochemistry

CHM 2210-U01 – ORGANIC CHEMISTRY I

Fall 2011

EXAM IV

Dr. Keller/Dr. Landrum

Version 2

Instructions: Choose the BEST answer to each multiple choice question.

Look over the Written Questions early during your test to be sure you allocate your time appropriately.

A)

Br

B) Br

H

D)

NH 2

C)

Br (^) NaNH 2 Excess Br^ Work-up

NH 4 Cl

CH 3

D

C

E) Na

A) B)

C) (^) D)

E) All are Equally stable

CH (^3)

D

H

Br

CH (^3)

D

Br

H

H

D

CH (^3)

Br

Br

D

CH (^3)

H

A) B)

C) (^) D)

E) Both B and D would be produced

  1. Hydroboration of alkenes A. occurs in a single step to produce a diol B. results in syn diols C. requires oxidation of the alkyl borane D. is not regioselective
  2. Which reagent will convert 2- butyne into cis -2- butene? A. H 2 (1atm), Pt B. Na/NH 3 (l) C. NaBH 4 D. H 2 (1 atm), Pd (BaSO 4 ), quinoline (Lindlar’s catalyst) E. 1) Li, NH 3 ; 2) NH 4 Cl
  3. The reaction below produces which product?
  4. Which product(s) is/are produced by hydrobromination of 5. Hydration of alkenes in dilute H 2 SO 4 involves A. protonation of the alkene in the 1st^ step B. addition of H 2 O in the 1 st^ step C. Nucleophilic attack of H 2 O on the alkene D. None of the above 6. Oxymercuration/demercuration of alkenes A. occurs via formation of the bridged (cyclic) mercurinium ion B. produces syn -addition of H 2 O to the double bond C. requires oxidation of the carbon mercury bond D. is not regioselective 7. Hydroboration of 1-methycyclopentene produces 8. Which alkene would be the most stable?

CH 3

OH

OH

CH (^3)

OH

CH (^3)

OH

CH (^3)

OH CH (^3)

OH

OH

A) (^) B)

C) (^) D)

E)

A)

B)

C)

D) E)

X (C 8 H 14 )

H 2

Pt

Y (C 8 H 16 )

OH OH

OH

OH

OH

A) B)

B) D)

E)

CH 3

CH 3

Br

  1. Why is the alkyl bromide shown below NOT capable of undergoing an E2 reaction upon treatment with sodium ethoxide?

A. Br -^ is too poor a leaving group. B. The substrate is too hindered. C. Too much angle strain would be present in the alkene product. D. Sodium ethoxide is a poor base to use in E reactions. E. The C-H and C-Br bonds which need to break cannot achieve anti-periplanar orientation.

  1. Which of the following reductions of an alkyne is NOT correct?

A. 2-Pentyne + 2H 2 /Pt  pentane B. 2-Pentyne + H 2 /Ni 2 B(P-2)  Z-2-Pentene C. 2-Pentyne + Li/NH 3 (l)  E-2-Pentene D. All of the above are correct. E. None of the above is correct.

  1. Based on the reaction below, one can conclude that compound X would include which of the following :

A. no rings and no double bonds. B. no rings and one double bond. C. one ring and one double bond. D. two rings and no double bonds. E. one triple bond.

  1. Which alcohol would be most easily dehydrated?
  2. Carbocations are intermediates in many reactions of alkenes and alcohols. Which of the following are possible reactions of carbocations?

A. rearrange to form a more stable carbocation. B. lose a proton to form an alkene. C. combine with a nucleophile. D. all of the above.

  1. On hydrogenation, a compound C 9 H 12 absorbs two moles of hydrogen. Which of the following is a possible structure for the compound?

A) B)

C) D)

E) None of the Above

OH Con H 2 SO^4 

A) A)

C) D)

E)

H

NaNH 2 CH 3 CH 2 Br^ H (^2) Ni 2 B (P-2) X

Br

A) B)

C) (^) D)

E)

  1. Which statement is true concerning the formation of alcohols by the hydroboration method?

A. Overall, the process results in syn addition and anti -Markovnikov orientation. B. Overall, the process results in anti addition and anti -Markovnikov orientation. C. Overall, the process results in syn addition and Markovnikov orientation. D. Overall, the process results in anti addition and Markovnikov orientation. E. The stereochemistry and orientation are unpredictable.

  1. Give the IUPAC name for the following compound:

A. (E)-4-ethyl-2,5-dimethyl-3-octene B. (Z)-4-ethyl-2,5-dimethyl-3-octene C. (E)-5-ethyl-4,7-dimethyl-5-octene D. (E)-4-ethyl-2,5-dimethyl-4-octene E. (Z)-5-ethyl-4,7-dimethyl-5-octene

  1. The structure of the product, X , formed in the following sequence of reactions would be:
    1. Which product would be formed in an appreciable amount when trans -1-bromo-2- methylcyclohexane undergoes dehydrohalogenation upon treatment with sodium ethoxide in ethanol?
    2. An alkene with the molecular formula C 8 H 16 undergoes ozonolysis to yield a mixture of (CH 3 ) 2 C=O and (CH 3 ) 3 CCHO. The alkene is:

A. 2,2-Dimethyl-2-hexene B. 2,3-Dimethyl-2-hexene C. 2,4-Dimethyl-2-hexene D. 2,4,4-Trimethyl-2-pentene E. More than one of the above is a possible answer

  1. Which alkene would you expect to be the major product of the following dehydration?

A) B)

C) D)

E)

O

O

H

H

H

Br

Br

H

H

Br

H

Br

H

Br

H

Br

I) II) III)

OH

Br

Br

OH

Br

Br

OH

Br

OH

OH

A) (^) B) C)

D) E)

C

Cl

Cl

A) CH 2 Cl 2 , t-BuOK

B) CHCl 3 , t-BuOK

C) CH 2 Cl 2 , NaBH 4

D) Cl 2 C N N, h

  1. An alkene with the molecular formula C 10 H 18 is treated with ozone and then with zinc and acetic acid. The sole product isolated from these reactions is:

What is the structure of the alkene?

  1. The reaction of Br 2 with cyclohexene would produce the compound(s) represented by structure(s):

A. I only B. II and III C. II only D.. III only E. I, II, and III

  1. Which of the following reactions of cyclobutene would yield a meso product?

A. Reaction with H 3 O+^ , H 2 O B. Reaction with Br 2 , CCl (^4) C. Reaction with Cl 2 , CCl (^4) D. Reaction with cold, dilute KMnO 4

  1. In general, Markovnikov’s Rule predicts that the addition of an unsymmetrical electrophilic reagent to an unsymmetrical alkene occurs regioselectivity because:

A. the product is statistically favored. B. steric hindrance favors its formation. C. it is formed via the more/most stable carbocation. D. it is the more/most rapidly produced product. E. All of the above are reasons.

  1. Which reagent would produce the following product from cyclohexene?
  2. Which reaction of an alkene proceeds with anti addition?

A. Hydroboration/oxidation B. Bromination C. Hydroxylation with cold KMnO 4 D. Hydrogenation E. Hydrochlorination (addition of HCl)

  1. Which of these could NOT be formed when cyclopentene reacts with an aqueous solution of bromine?
  1. Hg(OAc) 2 /H 2 O

  2. NaBH 4

OH

Br 2

Br

Br

KMnO 4 Cold, 0 C

OH

OH D

D

H H

D 2 /Pt

A)

B)

C)

D)

O

OH

O

O (^) O Mn O O

OH (^) OH

OH (^) OH OH^ OH

A)

B)

C)

D) E)

  1. What product would result from the following reaction?

dil. KMnO (^4)

cold

?

  1. Which reaction is regioselective?