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Midterm Exam 1 with Answer Key - Organic Chemistry II | CHM 2211, Exams of Organic Chemistry

University of Central Florida (UCF)Organic Chemistry
Prof. Jingdong Ye

jingdong ye Material Type: Exam; Professor: Ye; Class: Organic Chemistry II; Subject: Chemistry; University: University of Central Florida;

Typology: Exams

2011/2012

Uploaded on 04/05/2012

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CHM2211-0003 spring 2012 Instructor: Dr. Jingdong Ye
Midterm exam I
February 1, 2012
28 multiple choice questions, 28 points; exam duration: 50 min
choose only one correct and best answer for each multiple choice question, please use scantron.
1. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
II
III
H
HH
I
A) III>II>I
B) I>II>III
C) II>I>III
D) III>I>II
E) none of these
2. Which one of the following compounds will have the lowest wavenumber for carbonyl absorption?
OOOOO
III III IV V
A) I
B) II
C) III
D) IV
E) V
3. Which of the following alkene groups will produce the strongest signal?
FCl Br
III III IV
1
Name:
PID:
pf3
pf4
pf5
pf8
pf9
pfa

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CHM2211-0003 spring 2012 Instructor: Dr. Jingdong Ye

Midterm exam I

February 1, 2012 28 multiple choice questions, 28 points; exam duration: 50 min choose only one correct and best answer for each multiple choice question, please use scantron.

  1. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber. II III H H H I A) III>II>I B) I>II>III C) II>I>III D) III>I>II E) none of these
  2. Which one of the following compounds will have the lowest wavenumber for carbonyl absorption? O O^ O^ O^ O I II^ III^ IV V A) I B) II C) III D) IV E) V
  3. Which of the following alkene groups will produce the strongest signal? F (^) Cl Br

I II^ III^ IV

Name: PID:

A) I

B) II

C) III

D) IV

  1. Which one of the following compounds is consistent with the following IR spectrum? NH 2 CH 3 NHCH 3 NH 2 NH^2 CH 3 CH 3 N(CH 3 ) 2 I II^ III^ IV^ V A) I B) II C) III D) IV E) V
  2. Which one of the following compounds is consistent with the following IR spectrum?

A) 2-methylheptane B) 1-heptanol C) heptanamine D) 1-chloroheptane E) none of these

  1. Which of the following compounds will have a base peak at m/z=43? A) CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 B) (CH 3 CH 2 ) 2 CHCH 3 C) (CH 3 ) 3 CCH 2 CH 3 D) (CH 3 ) 2 CHCH(CH 3 ) 2 E) none of these
  2. Which of the following is expected to be the base peak in the mass spectrum of pentanal? CH 3 CH 2 CH 2 CH 2 CH O pentanal A) 29 B) 41 C) 44 D) 58 E) 86
  3. Calculate the degree of unsaturation for C 5 H 5 Br 2 NO? A) 4 B) 6 C) 2 D) 3 E) 7
  4. Protons Ha and Hb in the following compound are _________. OH Hb Ha A) homotopic B) enantiotopic C) diastereotopic D) mesotopic E) none of these
  5. How many signals would you expect to find in the 1 H NMR spectrum of the following compound? O O A) 4 B) 5 C) 6 D) 7 E) 8
  6. Which of the following protons appear most upfield in the 1 H NMR spectrum?

H H H II (^) III IV I H A) I B) II C) III D) IV E) none of these

  1. Which of the following compounds will display two triplets and a singlet in the 1 H NMR spectrum? A) CH 3 CH(OCH 3 ) 2 B) CH 3 OCH 2 CH 2 OCH 3 C) CH 3 OCH 2 CH(OH)CH 3 D) CH 3 OCH 2 CH 2 CH 2 CH 2 OCH 3 E) none of these
  2. Which of the following is the maximum multiplicity observed for Hc protons in the following compound? Assume that Jcd and Jcb values are different? H N a (^) b c d A) 5 B) 6 C) 8 D) 12 E) none of these
  3. Which of the following structures is consistent with this 1 H NMR spectrum? 1 1 5 3
  1. Which of the following compounds will not display a carbonyl carbon signal in the DEPT-90 and DEPT-135 13 C NMR spectroscopy? H O O O N H O I II^ III A) I B) II C) III D) II & III E) none of these
  2. Which of the following compounds is consistent with the following 13 C NMR spectrum? 80 70 60 50 40 30 20 10 0 PPM OH HO OH I II III OH IV A) I B) II C) III D) IV E) none of these
  3. Rank the following dienes in increasing order of stability (least to most). I II^ III^ IV C

A) I<IV<III<II

B) III<II<I<IV

C) IV<II<III<I

D) II<IV<III<I

E) I<III<II<IV

  1. Which one of the following represents the LUMO of 1,3, 5-hexatriene)? I (^) II III IV V A) I B) II C) III D) IV E) V
  2. Which major product(s) are formed for the following reaction? HI I I I I I (^) II III^ IV I V A) I B) II C) III D) IV E) V
  3. Which one of the following dienophiles is most reactive in the Diels-Alder reaction? OCH 3 I III IV O O O II V A) I B) II C) III D) IV E) V
  4. What diene and dienophile would react to give the following Diels-Alder product?

Midterm1Key: 1.B 2.D 3.A 4.B 5.B 6.C 7.B 8.B 9.A 10.D 11.C 12.D 13.C 14.B 15.D 16.D 17.D 18.B 19.B 20.D 21.C 22.C 23.D 24.A 25.C 26.D 27.C 28.A