organic chemistry

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Chemistry 332 (001) Spring 2019 Quiz 2 Questions and Corresponding Figures Quiz 2 is due on Canvas by 11:00 am Monday April 22 Please note that Dr. Walker and the GTAs cannot answer questions related to an active quiz, as this would impose an unfair disadvantage to the other members of the class. This includes questions about the wording and specific instructions of quiz questions. Thank you for your anticipated understanding. Important Notes § Solutions requiring the use of one or more universal constants must be based on the universal constants provided

in the Unit 1 lecture notes document § Solutions requiring the use of one or more electronegativity values must be based on those provided in Table 1.3

of Bruice (page 11) Question 1 [1 pt] A certain proton NMR spectrum exhibits one singlet, one quartet and a number of other peaks. The height of the singlet’s “integration step” is 43 mm while the quartet’s “integration step” is 196 mm. Given that the singlet is due to two protons how many protons (expressed as a whole number) are responsible for the quartet? Question 2 [1 pt] Based on the approach/notation/data presented in lecture what is the appropriate chemical shift increment for group B that must be used in the process for predicting the chemical shift of proton HA?

Question 3 [1 pt] Based on the approach/notation/data presented in lecture what is the appropriate chemical shift increment for group D that must be used in the process for predicting the chemical shift of proton HC? Question 4 [1 pt] Based on the approach/notation/data presented in lecture what is the appropriate chemical shift increment for group F that must be used in the process for predicting the chemical shift of proton HE? Question 5 [1 pt] Using the approach/notation/data presented in lecture what is the predicted chemical shift of proton HG in ppm? Please provide just the numerical value, expressed with one decimal place, along with an asterisk if appropriate. Do not include units.

Question 6 [1 pt] Using the approach/notation/data presented in lecture what is the predicted chemical shift of proton HJ in ppm? Please provide just the numerical value, expressed with one decimal place, along with an asterisk if appropriate. Do not include units. Question 7 [1 pt] Using the approach/notation/data presented in lecture what is the predicted chemical shift of proton HK in ppm? Please provide just the numerical value, expressed with one decimal place, along with an asterisk if appropriate. Do not include units.

Group B

HA O

H Group D

HC OBr

Group F

N HE

H

HG

CCl CH2CH2CH(CH3)2 HJ

C

OH

C N

HK

CHS CH3

OCH2CH2CHBr2

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Question 8 [1 pt] What type of proton NMR signal will proton HL give rise to?

Question 9 [1 pt] What type of proton NMR signal will proton HM give rise to? Question 10 [1 pt] What type of proton NMR signal will proton HN give rise to? Question 11 [1 pt] How many unique signals will be exhibited in the proton NMR spectrum of compound O?

Compound O Compound P Compound Q Question 12 [1 pt] How many unique signals will be exhibited in the proton NMR spectrum of compound P? Question 13 [1 pt] How many unique signals will be exhibited in the proton NMR spectrum of compound Q? Question 14 [1 pt] What is the degree of unsaturation of a compound whose molecular formula is C11H21N? Question 15 [2 pts] Which one of the following statements is correct? Spectra I and II are provided on page 3.

Compound X Compound Y

¨ Spectra I and II are due to compounds X and Y respectively ¨ Spectra I and II are due to compounds Y and X respectively

HL HM

SCH3

HN

Cl Cl S

CH2CH3

H

Cl

CH3

O

CH3H

CH3

N N

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