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10 Solved Questions - Examination 3 | CHEM 2411, Exams of Organic Chemistry

Clayton State UniversityOrganic Chemistry

Material Type: Exam; Class: Organic Chemistry I; Subject: Chemistry; University: Clayton State University; Term: Unknown 1989;

Typology: Exams

Pre 2010

Uploaded on 08/18/2009

koofers-user-ldj
koofers-user-ldj 🇺🇸

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Chem 2411
Clower
Exam 3 review
1. Circle the best answer from each of the following sets of molecules.
(a) The best nucleophile in a substitution reaction at a primary carbon.
(b) The least reactive compound in a SN1 reaction.
2. Decide if each of the following substitution reactions will proceed by an SN1 or SN2
mechanism, and draw the major product of each reaction, showing appropriate stereochemistry.
(a)
(b)
(c)
(d)
acetic acid
+
Br NaOCH2CH3
ethanol
+ NaCN
DMSO
Br
methanol
(CH3)3CCl CH3CO2H
I
pf3
pf4

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Clower Exam 3 review

  1. Circle the best answer from each of the following sets of molecules. (a) The best nucleophile in a substitution reaction at a primary carbon. (b) The least reactive compound in a SN1 reaction.
  2. Decide if each of the following substitution reactions will proceed by an SN1 or SN 2 mechanism, and draw the major product of each reaction, showing appropriate stereochemistry. (a) (b) (c) (d) acetic acid

Br (^) NaOCH 2 CH 3 ethanol

  • NaCN DMSO Br methanol (CH 3 ) 3 CCl CH 3 CO 2 H I

Clower Exam 3 review

  1. Which methyl halide is the most polar? ______________
  2. Propose a detailed mechanism for the solvolysis reaction of R-2-bromobutane with methanol. Include all appropriate mechanistic arrows, intermediates, and stereochemistry.

Clower Exam 3 review

  1. (a) Draw a Fischer projection of (2 R ,3 S )-dibromobutane. (b) How many total stereoisomers exist for 2,3-dibromobutane? ____________ (c) Is 2,3-dibromobutane a geminal or a vicinal dihalide? ____________ (d) Is (2 R ,3 S )-dibromobutane optically active? ____________
  2. Determine whether the two structures in each of the following pairs represent constitutional isomers, enantiomers, diastereomers, or identical compounds. (a) ( S )-1-ethyl-1,2,2-trimethylcyclopropane (b) (c) H 3 C CH 2 OH H H OH HO H 3 C OH CH 2 OH HO H H CHO HO H CH 3 HO H CHO H OH CH 3 H OH CH 3 CH 2 CH 3 CH 3 CH 3