Assignment Research Writer
  • Our services
    • Home
  • Home
  • My account
  • Order now
Order Now
Uncategorized

organic

4 min read
Posted on 
February 3rd, 2023
Home Uncategorized organic

instructions attached

Massachusetts Institute of Technology 5.12, Spring 200

Don't use plagiarized sources. Get Your Custom Essay on
organic
Just from $13/Page
Order Essay

5

Problem Set #

1

Due: February 10, 4:00 pm

1. Assign formal charges to each atom below (a formal charge of zero is assumed if
no charge is indicated). Cross out the configurations that are not reasonable, and
provide an explanation (large charge – greater than +/- 1, incomplete octet, octet
exceeded).

Br C C N

O C O N

NO H

O

O F B N

2. Reorient the molecule at the left to match the partially drawn perspective at the
right. Complete the drawing at the right by adding the two missing substituents at their
correct positions. Build a model if necessary.

CH2CH

3

F
a) F
H3C H H

H
CH3b) F CH2CH3 H CH2

CH3

1

Massachusetts Institute of Technology 5.12, Spring 2005

3. Provide Kekulé structures for the following molecules, including all major resonance
contributors (no more than 2 formal charges, no formal charge greater than +/- 1).

a) N2

b) CH3CO2Na

c) O3

4. Label all of the functional groups in amoxicillin, an antibiotic from the penicillin
family.

O

H
N

N

S

O

NH2 CH3
CH3

HO O
HO

2

Massachusetts Institute of Technology 5.12, Spring 2005

5. Provide orbital drawings of the following molecules. (Don’t forget to shade the p
orbitals appropriately!) Indicate the hybridization and bond angle at each non-
hydrogen atom. Indicate the sigma and pi bonds and all lone pairs of electrons.

a) BeCl2

b) H2C C O

3

Massachusetts Institute of Technology 5.12, Spring 2005

6. Circle the following pairs of structures that do not constitute resonance structures.
For the proper resonance pairs, draw curved arrows to convert the first structure to the
second. Draw in all lone pairs of electrons.

CH3H3C CH3H3CN N
a)

b) H2C C CH2 H3C C CH

O Oc)

S S
d) H3C C CH2 H3C C CH2H H

O OH

e)

CH3 H3C CH2H3C

4

Massachusetts Institute of Technology 5.12, Spring 2005

7.

Smith, Janice G. Organic Chemistry. 1st ed. New York, NY: McGraw-Hill,
2006, p. 77. ISBN: 0072397462.

8. When you ingest aspirin, it passes through your stomach, which has an acidic pH,
before traveling through the basic environment of your intestine. Provide the correct
structure of aspirin a) as it exists in the stomach and b) as it exists in the intestine.

O

O 3

O

O
H

CH

aspirin

5

Massachusetts Institute of Technology 5.12, Spring 2005

9. Rank the following sets of molecules according to acidity (1= most acidic). Explain
your choices.

H Cl H H Cl H H H H
a) H C C C H H C C C H Cl C C C H

H Cl H H H H H H H

H Hb) H

3CH
N N

H3C H3C CH3

c) HCl H2O H2S

O
O O H

Hd) H2C H2C H H2CN NO H
H

H
H

C C HC He) C
HH

10. Rank the following molecules according to basicity ( 1 = most basic). Explain.

H2C N CH3 H3C N CH3H3C C N
H

6

Massachusetts Institute of Technology 5.12, Spring 2005

11. Rank the molecules in order of acidity (1 = most acidic). Explain your answer by
drawing all resonance contributors of each conjugate base. Use the back of this page,
if necessary.

OH
OH OH

O2NNO2

7

Massachusetts Institute of Technology 5.12, Spring 2005

12. Rank the hydrogen atoms (Ha, Hb, Hc) in the following molecules according to
acidity.

Ha O O
H2C
CH3 Ha Hc

Hb H H Hc Hb

___ > ___ > ___ ___ > ___ > ___

13. Circle the most acidic H atom in ascorbic acid (vitamin C).

O
O

OH
HO

HO
OH

14.

Smith, Janice G. Organic Chemistry. 1st ed. New York, NY: McGraw-Hill,
2006, p. 77. ISBN: 0072397462.

8

Massachusetts Institute of Technology 5.12, Spring 2005

15. Draw the products of each reaction. Show all lone pairs in reactants and
products. Circle the side of the reaction that is favored at equilibrium.

a) H C C H Li CH2CH3

O
b) OCH2CH3F3C OH

c) CH3CH2NH2 CH3CH2S

d) CH3CH2SH2 CH3CH2OH

NH3 OH

e)

9

Massachusetts Institute of Technology 5.12, Spring 2005

16. Draw in all lone pairs and provide the product of each reaction. Use curved arrow
notation to show the mechanism. Show all resonance contributors of reactants and
products, if applicable.

a) H2O

Cl
b) Cl CH3Al

Cl Cl

O
c) OH

ClH3C

d)
HS

CH3
e) NH C C

CH3

H
f) H Cl

H
Hint: find nucleophile (electron rich)
and electrophile (electron poor).

O
g)

H3C OH

10

Order an Essay Now & Get These Features For Free:

Turnitin Report

Formatting

Title Page

Citation

Outline

Place an Order
Share
Tweet
Share
Tweet
Calculate the price
Pages (275 words)
$0.00
Assignment Research Writer
Company
Legal
  • Home
How Our Service is Used:
Assignment Research Writer essays are NOT intended to be forwarded as finalized work as it is only strictly meant to be used for research and study purposes. Assignment Research Writer does not endorse or condone any type of plagiarism.
Subscribe
No Spam
  • Home
© 2023 Assignment Research Writer. All rights reserved.
Assignment Research Writer will be listed as ‘Assignment Research Writer’ on your bank statement.