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Organic Chemistry 2 Exam Study Guide with Answers/Explanations, Study notes of Organic Chemistry

I took some questions that my professor provided on the study guide and try to explain the write answer to the best of my knowledge in preparation for the exam.

Typology: Study notes

2022/2023

Available from 04/11/2023

kelli-mitchell
kelli-mitchell 🇺🇸

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1. What is the correct IUPAC name of the following compound?
a. 2-isopropylbutanal
b. 2-ethyl-3-methylbutanal
c. 2-isopropylbutanone
d. 3-ethyl-2-methylbutanal
Correct Answer: B
Explanation: When naming aldehydes, you always want to change the -e from the
parent name to -al. For example, hexane will be switched to hexanal if an aldehyde is
present. We can already eliminate c, because we are not dealing with any ketones as
our functional group. You always want to start where the carbonyl double bond is, so
that would be 1.
Now that the compound is number look at the answer choices. A cannot be the answer
because there is no isopropyl group on carbon 2. Also, it’s missing the other
substituent of carbon 3. Answer choice B, makes the most since, because answer
choice D would mean that the carbonyl double would not be given the smallest
number. You can never assign the larger number to the aldehyde, ketone, double bond,
or triple bond; always try to give it the smallest number.
2. Rank the compounds in order of decreasing reactivity with LiAlH4
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  1. What is the correct IUPAC name of the following compound?

a. 2-isopropylbutanal

b. 2-ethyl-3-methylbutanal

c. 2-isopropylbutanone

d. 3-ethyl-2-methylbutanal

Correct Answer: B

Explanation: When naming aldehydes, you always want to change the -e from the

parent name to -al. For example, hexane will be switched to hexanal if an aldehyde is

present. We can already eliminate c, because we are not dealing with any ketones as

our functional group. You always want to start where the carbonyl double bond is, so

that would be 1.

Now that the compound is number look at the answer choices. A cannot be the answer

because there is no isopropyl group on carbon 2. Also, it’s missing the other

substituent of carbon 3. Answer choice B, makes the most since, because answer

choice D would mean that the carbonyl double would not be given the smallest

number. You can never assign the larger number to the aldehyde, ketone, double bond,

or triple bond; always try to give it the smallest number.

  1. Rank the compounds in order of decreasing reactivity with LiAlH

a. A>B>D>C b. B>C>A>D c. A>D>C>B d. D>A>C>B Correct Answer: C Explanation: Lithium Aluminum hydride is very reactive; it will react with all of the carboxylic acid and its derivatives. Acid chloride is highly reactive, so that would be the first, so we can eliminate answer choices b and d. Looking at the choices, we have an ester, ketone, and aldehyde. Out of the three, aldehyde is more reactive so that will take second place. Ketone will take third and ester will be the least reactive in this order of ranking.

  1. What is the major product of the following reaction? Correct Answer: D Explanation: With the way my professor teaches, when it comes to problems like this it's important to memorize and understand the functional groups. Looking at the carbon indicated by the blue square, it can be identified that the functional group is an acetal/ketal. Since we have oxygen and alcohol, I remember to only convert the alcohol into an ester. If it was an ester with an oxygen bonded to the same carbon, the ester will then be converted to an alcohol. Remember functional groups!!!

The OH on the other carbon would be left alone. Choice A does not make sense, because only a carboxylic acid can change into an acid chloride with SOCl2.