CHM 2200C EXAMINATION 4A April 13, 2001
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1 M 2200 EXAMINATIN 4A April 13, 2001 INSTRUTINS: Be sure that you have 3 pages with problems, one double-sided answer sheet, and one blank sheet for scratch work. In the spaces provided on the answer sheet, print your name and sign your name on both sides of the answer sheet; put the last 4 digits of your social security number, laboratory section number, and seat number on the front of the answer sheet. Put your answers neatly in the spaces provided on the answer sheet. NLY TE ANSWER SEET WILL BE LLETED FR GRADING. NTE: The SUSSAI/SIRS forms for Dr. ilinski will be administered during lecture on Wednesday, April 18, [16] For each of the following compounds, provide a name. Be sure to give cis or trans when it is necessary. Be sure to give D or L when it is necessary. Be sure to give " or $ when necessary. _ (a) ( N l (b) 3 N 2 (c) (d) [16 points] For each of the following, provide a structural formula. The structural formulas which you give may be condensed structural formulas. Be sure to indicate cis or trans when it is necessary. Be sure to indicate D or L when it is necessary. Be sure to indicate " or $ when necessary. (a) isobutylisopropylamine (b) N,N-diphenylbenzamide (c) the less stable chair conformation of cis-1,3-dimethylcyclohexane (d) a Fischer projection formula of the open form of D-fructose 3. [10 points] onsider the structure given on the ANSWER SEET. (a) ircle clearly each tetrahedral stereocenter. [Note that your score for this problem will be based on the number of correct answers minus the number of incorrect answers which you give.] (b) What is the maximum number of stereoisomers possible for this structure? 4. [12] Stereoisomers of tartaric acid are shown to the right. (a) ()-Tartaric acid is the D stereoisomer and has a melting point of 170 o. Which structure (A, B, or ) is ()-tartaric acid? (b) Will compound rotate plane-polarized light in (i) a dextrorotatory direction, (ii) a levorotatory direction, (iii) an unknown direction, or (iv) in no direction? A B (c) Will a solution containing equal amounts of compound A and compound B rotate plane-polarized light in (i) a dextrorotatory direction, (ii) a levorotatory direction, (iii) an unknown direction, or (iv) in no direction? (d) Is the melting point of compound (i) the same as compound A or (ii) different from compound A? 2 2
2 M 2200 EXAMINATIN 4A April 13, 2001 Page 2 5. [24 points] onsider the aworth projection formula of compound D shown to the right. ompleting clearly the structures in the spaces given on your ANSWER SEET, provide each of the following. (a) the chair conformation for compound D (b) the Fischer projection formula for the open form of compound D (c) a aworth projection formula for the anomer of compound D (d) a aworth projection formula for an epimer of compound D which is not the anomer of compound D (e) the chair conformation for a diastereomer of compound D which is not an epimer of compound D (f) a aworth projection formula for the enantiomer of compound D 2 compound D 6. [6 points] onsider the following equilibrium. _ N 2 ( N ( N N 2 (a) Does this equilibrium lie to the left or to the right? (b) Is the base soluble or insoluble in water? (c) Is the conjugate acid soluble or insoluble in water? 7. [16] Provide a structural formula for each of the major organic products in the following reactions. You need not worry about geometric isomers. (a) 3 2 N 3 l 2 (b) N 3 l 2 (c) (d) 3 2 N 3 Na 3 2 l 2 3 N 2 2
3 M 2200 EXAMINATIN 4A April 13, 2001 Page 3 Approximate pk a Values (relative to 2 ; A = acid; A = conjugate base) entry A pk a A entry A pk a A 1 I 10 I N N 2 2 Br 9 Br [ ] 3 l 7 l 25 P P F 3 S 3 6 F 3 S S 4 5 S 4 26 ( ) ( ) 2 27 (N 2 ) 2 =N 2 13 (N 2 ) 2 =N N N 7 S 4 2 S P P F 3.5 F ( 3 ) 2 17 ( 3 ) 2 11 PhN N (pyridinium) PhN 2 33 ( 3 18 ( N P 4 7 P / 26 / 15 2 S 7 S PhS 7 PhS 38 N 3 36 N 2 17 N 4 9 N 3 39 Ph 3 41 [Ph 2 ] 18 ( 3 ) ( 3 ) = 3 43 [ 2 = 2 ] 19 N 9 N 41 Ph 43 Ph 20 Ph 10 Ph 42 2 = 2 45 [ 2 =] [ 3 2 ] 22 3 S 11 3 S
4 M 2200 EXAMINATIN 4A Printed Name: ANSWER SEET April 13, 2001 Lab Section No.: Signed Name: Last 4 Digits Soc. Sec. No.: Seat No.: 1 [16] 2 [16] 3 [10] 4 [12] 5 [24] 6 [6] 7 [16] TTAL [100] 1a 1b 1c 1d 2a 2b 2c 2d 3a a 4b 4c 3b 4d
5 M 2200 EXAMINATIN 4A Printed Name: ANSWER SEET April 13, 2001 Signed Name: 5a 5b 5c d 5e 5f a 6b 6c 7a 7b 7c 7d
6 M 2200 EXAMINATIN 4B April 13, 2001 INSTRUTINS: Be sure that you have 3 pages with problems, one double-sided answer sheet, and one blank sheet for scratch work. In the spaces provided on the answer sheet, print your name and sign your name on both sides of the answer sheet; put the last 4 digits of your social security number, laboratory section number, and seat number on the front of the answer sheet. Put your answers neatly in the spaces provided on the answer sheet. NLY TE ANSWER SEET WILL BE LLETED FR GRADING. NTE: The SUSSAI/SIRS forms for Dr. ilinski will be administered during lecture on Wednesday, April 18, [16] For each of the following compounds, provide a name. Be sure to give cis or trans when it is necessary. Be sure to give D or L when it is necessary. Be sure to give " or $ when necessary. _ (a) ( N Br (b) 2 (c) 2 (d) 3 N 2 2. [16 points] For each of the following, provide a structural formula. The structural formulas which you give may be condensed structural formulas. Be sure to indicate cis or trans when it is necessary. Be sure to indicate D or L when it is necessary. Be sure to indicate " or $ when necessary. (a) sec-butylisopropylamine (b) N,N-diphenylbenzamide (c) a Fischer projection formula of the open form of D-fructose (d) the more stable chair conformation of cis-1,3-dimethylcyclohexane 3. [10 points] onsider the structure given on the ANSWER SEET. (a) ircle clearly each tetrahedral stereocenter. [Note that your score for this problem will be based on the number of correct answers minus the number of incorrect answers which you give.] (b) What is the maximum number of stereoisomers possible for this structure? 4. [12] Stereoisomers of tartaric acid are shown to the right. (a) ()-Tartaric acid is the D stereoisomer and has a melting point of 170 o. Which structure (A, B, or ) is ()-tartaric acid? (b) Is the melting point of compound (i) the same as compound A or (ii) different from compound A? (c) Will a solution containing equal amounts of compound A and A B compound B rotate plane-polarized light in (i) a dextrorotatory direction, (ii) a levorotatory direction, (iii) an unknown direction, or (iv) in no direction? (d) Will compound rotate plane-polarized light in (i) a dextrorotatory direction, (ii) a levorotatory direction, (iii) an unknown direction, or (iv) in no direction? 2 2
7 M 2200 EXAMINATIN 4B April 13, 2001 Page 2 5. [24 points] onsider the aworth projection formula of compound D shown to the right. ompleting clearly the structures in the spaces given on your ANSWER SEET, provide each of the following. (a) the chair conformation for compound D (b) the Fischer projection formula for the open form of compound D (c) a aworth projection formula for the anomer of compound D (d) a aworth projection formula for an epimer of compound D which is not the anomer of compound D (e) the chair conformation for a diastereomer of compound D which is not an epimer of compound D (f) a aworth projection formula for the enantiomer of compound D 2 compound D 6. [6 points] onsider the following equilibrium. _ N 2 ( N ( N N 2 (a) Does this equilibrium lie to the left or to the right? (b) Is the conjugate acid soluble or insoluble in water? (c) Is the base soluble or insoluble in water? 7. [16] Provide a structural formula for each of the major organic products in the following reactions. You need not worry about geometric isomers. (a) (b) 3 2 N N 3 Na 2 l 2 (c) 3 2 l 2 3 N 2 (d) N 3 l 2
8 M 2200 EXAMINATIN 4B April 13, 2001 Page 3 Approximate pk a Values (relative to 2 ; A = acid; A = conjugate base) entry A pk a A entry A pk a A 1 I 10 I N N 2 2 Br 9 Br [ ] 3 l 7 l 25 P P F 3 S 3 6 F 3 S S 4 5 S 4 26 ( ) ( ) 2 27 (N 2 ) 2 =N 2 13 (N 2 ) 2 =N N N 7 S 4 2 S P P F 3.5 F ( 3 ) 2 17 ( 3 ) 2 11 PhN N (pyridinium) PhN 2 33 ( 3 18 ( N P 4 7 P / 26 / 15 2 S 7 S PhS 7 PhS 38 N 3 36 N 2 17 N 4 9 N 3 39 Ph 3 41 [Ph 2 ] 18 ( 3 ) ( 3 ) = 3 43 [ 2 = 2 ] 19 N 9 N 41 Ph 43 Ph 20 Ph 10 Ph 42 2 = 2 45 [ 2 =] [ 3 2 ] 22 3 S 11 3 S
9 M 2200 EXAMINATIN 4B Printed Name: ANSWER SEET April 13, 2001 Lab Section No.: Signed Name: Last 4 Digits Soc. Sec. No.: Seat No.: 1 [16] 2 [16] 3 [10] 4 [12] 5 [24] 6 [6] 7 [16] TTAL [100] 1a 1b 1c 1d 2a 2b 2c 2d 3a a 4b 4c 3b 4d
10 M 2200 EXAMINATIN 4B Printed Name: ANSWER SEET April 13, 2001 Signed Name: 5a 5b 5c d 5e 5f a 6b 6c 7a 7b 7c 7d
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