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Organic Chemistry I Midterm #1, Fall 2015 - Prof. Chrysoula Vasileiou, Exams of Organic Chemistry

A midterm examination for the organic chemistry i course offered at carnegie mellon university in the fall of 2015. Instructions for the exam, a list of questions with corresponding points and possible answers, and a scratch sheet for use during the exam. The questions cover various topics in organic chemistry, such as compound identification, orbital hybridization, formal charge assignment, and resonance structures.

What you will learn

  • What orbitals are used to form each indicated bond in the document?
  • What is the hybridization of the Sulfur atom in compound A?
  • What is the hybridization of the Nitrogen atom in compound A?
  • What are the names of the compounds provided in the document?
  • How many ฯ€-electrons are there in compound A?

Typology: Exams

2014/2015

Uploaded on 10/14/2015

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CEM251, Fall 2015
Midterm #1
1
FALL 2015
CEM 251: Organic Chemistry I
Sections 25-36, 39
TUE-THU 8:00 โ€“ 9:20 AM
September 29, 2015
This is a closed book and note examination. If boxes are provided for your
answers, only what is written in the boxes will be graded. You have 80 min to
complete the test.
Question
Points
Score
1
10
2
20
3
8
4
10
5
18
6
4
7
8
8
22
Bonus
10
Total
100
Section 25 Thu 10:20 โ€“ 11:10 AM Liz
Section 26 Thu 10:20 โ€“ 11:10 AM Jun
Section 27 Mon 12:40 โ€“ 1:30 PM Ding
Section 28 Mon 9:10 โ€“ 10:00 AM Ding
Section 29 Tue 10:20 โ€“ 11:10 AM Wei
Section 30 Thu 1:50 โ€“ 2:40 PM Wei
Section 31 Thu 4:10 โ€“ 5:00 PM Jun
Section 32 Tue 3:00 โ€“ 3:50 PM Yi
Section 33 Tue 4:10 โ€“ 5:00 PM Yi
Section 34 Thu 4:10 โ€“ 5:00 PM Tanner
Section 35 Thu 3:00 โ€“ 3:50 PM Jun
Section 36 Thu 1:50 โ€“ 2:40 PM Liz
Section 39 Wed 10:20 โ€“ 11:10 AM Rob
Section:____________
TA: _______________
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pf4
pf5
pf8
pf9
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Midterm #

FALL 2015

CEM 251: Organic Chemistry I

Sections 25-36, 39

TUE-THU 8:00 โ€“ 9:20 AM

September 29, 201 5

This is a closed book and note examination. If boxes are provided for your answers, only what is written in the boxes will be graded. You have 80 min to complete the test.

Question Points Score

Bonus 10

Total 100

Section 25 Thu 10:20 โ€“ 11:10 AM Liz Section 26 Thu 10:20 โ€“ 11:10 AM Jun Section 27 Mon 12 : 40 โ€“ 1 : 3 0 PM Ding Section 2 8 Mon 9:10 โ€“ 10:00 AM Ding Section 29 Tue 10:20 โ€“ 11:10 AM Wei Section 30 Thu 1:50 โ€“ 2:40 PM Wei Section 31 Thu 4:10 โ€“ 5:00 PM Jun Section 32 Tue 3:00 โ€“ 3:50 PM Yi Section 33 Tue 4:10 โ€“ 5:00 PM Yi Section 34 Thu 4:10 โ€“ 5:00 PM Tanner Section 35 Thu 3:00 โ€“ 3:50 PM Jun Section 36 Thu 1:50 โ€“ 2:40 PM Liz Section 3 9 Wed 10:20 โ€“ 11:10 AM Rob Name:______________________________ PID: _______________________________ Section:____________ TA: _______________

Midterm #

  1. Provide a name or a structure for the following compounds ( 10 pts, 2 pts each box ). a. 3 - chloro- 6 - nitro-octane b. c. 1 bromo, 3 hydroxy cyclopentane d e. 6 ethyl, 2,6 dimethyl, nonane 1 - fluoro, 2-isopropyl cyclohexane 5 amino, 2 bromo heptane

F

Br NH 2 Cl NO 2

Br

OH

Midterm #

  1. Answer the following questions about compound A (10 pts): a. Which of the atoms in compound A is the most electronegative? (2 pts) F b. What is the hybridization of the Nitrogen atom? (2 pts) sp 3 c. What is the hybridization of the Sulfur atom? (2 pts) sp 3 d. How many ฯ€ - electrons are there in compound A? (2 pts) 12 ฯ€ - electrons (6 ฯ€ - bonds) e. How many methyl groups (-CH 3 ) are there in compound A? (2 pts) 7 O N O Br SH Cl F A

Midterm #

  1. Draw 3 valid resonance structures for each of the following molecules (1 8 pts, 3 pts / box) N H O O N H O N H O N H O O O O

Midterm #

  1. Circle the correct answer. (2 2 pts, 2 pts each) a. Which of the following an iso-butyl group? b. Which is the correct electronic configuration for 7 N? c. Which of the following is the correct stick structure of the condensed structure on the left? d. Which of the following is NOT a correct set of resonance structures? e. Which of the following highlighted protons is MORE acidic? (circle the structure with the most acidic proton) 1s^2 2s^2 2px^2 2py^1 2pz^0 1s^2 2s^2 2px^2 2py^2 2pz^2 1s^2 2s^2 2px^1 2py^1 2pz^1 1s^2 2px^2 2py^2 2pz^1 O O O O O O O O O O O O O O O O CH 3 CH 2 CHCHCCH 2 CH 3 CH 2 CH 3 Cl CH 3 CH 3 Cl Cl Cl Cl O H (^) O H O H O^ H

Midterm # f. How many sp 2

- hybridized atoms are there in the following molecule? g. Which of the following is the correct molecular formula of the molecule below? h. Which of the following is the LEAST STABLE Newman projection? i. How many ฯ€-bonds are there in the following structure? j. What is the correct molecular formula of the following molecule? k. Looking down the C1-C2 bond, which one is the โ€œGaucheโ€ Newman projection of 1chloropropane? HN O C 9 H 14 NO (^) C 9 H 13 NO C 8 H 13 NO (^) C 8 H 12 NO O O N (^) a. 4 b. 5 c. 6 d. 7 H H H H H H H H Br CH 3 H H Br H H H H CH 3 OH H H Cl H H a. 3 b. 4 c. 5 d. 6 O OH N H a. C 9 H 10 O 2 N b. C 9 H 13 O 2 N c. C 8 H 13 O 2 N d. C 8 H 10 O 2 N CH 3 H H Cl H H H CH 3 H H H Cl H H 3 C H Cl H H H 3 C H H H H Cl

Midterm # Scratch Sheet : Needs to be turned in with the test (if missing, the test will not be graded)

  • Midterm #