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Organic Chemistry Midterm 1 - Lewis Structures and Bonding, Slides of Organic Chemistry

Webster UniversityOrganic Chemistry

A midterm exam from an Organic Chemistry course, focusing on Lewis structures, bonding, and resonance. Students are required to identify incorrect structures, convert formulas, determine formal charges, identify resonance structures, and determine if compounds are isomers or not. The exam also covers the determination of the number of sigma and pi bonds in a molecule, ranking hydrogen acidity, identifying the strongest acid and base, and polar vs non-polar molecules.

What you will learn

  • What is the pKa for a compound with Ka = 10-14?
  • Circle any of the following species which contain a carbon atom with a +1 formal charge.
  • Which of the following would not be a Lewis structure of CH3NO2?
  • Which is the appropriate conversion from condensed formula to skeletal formula?
  • Circle the compound that is the strongest acid.
  • Circle the compound that is the strongest base.

Typology: Slides

2021/2022

Uploaded on 09/27/2022

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Ch 334 Code _________
Midterm #1
October 13, 2006
1. (3 pts) Which of the following would not be a Lewis structure of CH3NO2?
Circle your choice.
2. (3 pts) Which is the appropriate conversion from condensed formula to skeletal
formula? Circle the correct answer.
CH
3CHClCH2CH(CH3)2
pf3
pf4
pf5
pf8

Partial preview of the text

Download Organic Chemistry Midterm 1 - Lewis Structures and Bonding and more Slides Organic Chemistry in PDF only on Docsity!

Ch 334 Code _________ Midterm # October 13, 2006

  1. (3 pts) Which of the following would not be a Lewis structure of CH 3 NO 2? Circle your choice.
  2. (3 pts) Which is the appropriate conversion from condensed formula to skeletal formula? Circle the correct answer.

CH 3 CHClCH 2 CH(CH 3 ) (^2)

  1. (3 pts) Convert the following skeletal formula to a condensed formula. Place your answer in the box provided.
  2. (4 pts) Circle any structures below that are resonance structures for the anion in the box.
  3. (10 pts) Determine whether the following pairs of compounds are isomers, resonance structures or neither. Lone pairs are not drawn on these structures. Place your answers in the blanks provided.

______________________

______________________

______________________

  1. (5 pts) Circle any of the following species which contain a carbon atom with a + formal charge. (All nonbonded electrons and electron pairs have been drawn in.)
  2. (3 pts) Circle any of the following species has a trigonal planar structure with 120 ° bond angles around the labeled carbon atom.
  3. (3 pts) How many hydrogens are present around each of the indicated carbon atoms?

Ca ______ Cb ______ Cc ______

  1. ( 3 pts) Which of the following statements correctly describes the typical bonding of carbon, nitrogen and oxygen in organic molecules? Circle it.

A. Oxygen participates in 2 covalent bonds and has 2 lone pairs of electrons

B. Nitrogen participates in 2 covalent bonds and has 1 lone pair

C. Carbon participates in 4 covalent bonds and has no lone pairs

D. Oxygen participates in 2 covalent bonds and has 2 lone pairs of electrons and Nitrogen participates in 2 covalent bonds and has 1 lone pair

E. Oxygen participates in 2 covalent bonds and has 2 lone pairs of electrons and Carbon participates in 4 covalent bonds and has no lone pairs

  1. ( 3pts) Consider the organic molecule drawn below. Describe which orbitals are used to form the C=O bond. Since there are two bonds, you must identify two different sets of orbitals. Circle the best response.

A. Csp^2 - Osp^2 and Cs - Op B. Csp - Osp and Cp - Op C. Csp^2 - Osp^2 and Cs - Os D. Csp^2 - Osp^2 and Cp - Op

  1. (4 pts) How many sigma and pi bonds are there in H 2 C=CH-C≡N?

There are ______ sigma bonds and ______ pi bonds.

  1. (4 pts) Consider the following molecule having three labeled protons, Ha, Hb , and Hc. Rank these protons in order of increasing acidity.

The most acidic hydrogen labeled is ________

The least acidic hydrogen labeled is _________

  1. (4 pts) Circle the compound that is the strongest acid.
  2. (3 pts) Circle any of the following that can be a Lewis acid.
  1. (3 pts) Circle the compound that is the strongest base.

A. NH 2 - B. OH- C. Cl - D. NH 3 E. I -

  1. (3 pts) Circle the compound which is the strongest Bronsted-Lowry acid?

A. H 2 S B. H 2 O C. NH 3

  1. (2 pts) Give two requirements a molecule must meet to be a polar molecule.

a.

b.

  1. (5 pts) Determine if the following molecules will be polar or non-polar. Give a reason for your choice. No correct reason, no credit.

Polar or Non Polar Reason

a. H 2 O

b. CO 2

c. Cl 2 O

d. BeClF

e. CH 4

  1. (4 pts) Identify the major functional groups in the following molecules. The best response is :

________

  1. A: aldehyde; B: amine; C: ether; D: ketone
  2. A: carboxylic acid; B: amine; C: ether; D: ketone
  3. A: carboxylic acid; B: amine; C: ester; D: ketone
  4. A: carboxylic acid; B: alkane; C: ether; D: ketone
  5. A: carboxylic acid; B: amine; C: ether; D: aldehyde