Deck 10: Organohalides

Question 1

Draw: trans-1-chloro-3-sec-butylcyclohexane

Answer 1

Question 2

Exhibit 10-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-3.Label the chirality centers in the monochlorination products of methylcyclopentane with an asterisk.

Answer 2

Question 3

Exhibit 10-2
To answer the following question(s) consider the reaction below:


-The original question has been combined with question #9 as part
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Answer 3

It appears that you are referring to a specific question from a test or textbook related to a chemical reaction, and you've provided a reference code
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If you have the actual content of the question or details about the chemical reaction, please provide them, and I would be happy to help with an answer. Otherwise, it is not possible to answer a question without knowing what the question is.

Question 4

The following compound has been used as a less-ozone-depleting replacement for Freons.Name this compound.
CHF₂CF₃

Question 5

Exhibit 10-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-3.Draw all the monochlorination products of methylcyclopentane (ignore stereoisomers).

Question 6

Exhibit 10-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-3.Tell whether radical chlorination of methylcyclopentane is an oxidation or a reduction process.

Question 7

Exhibit 10-2
To answer the following question(s) consider the reaction below:


-The original question has been combined with question #9 as part
b.This placeholder question is here to maintain the integrity of the numbering system between the printed copy and ExamView.Therefore,it has been marked "do not use on test" in ExamView's question information dialog.As a result,this placeholder question is automatically prevented from being chosen as a test question.

Question 8

Draw the skeletal structure of the product if the following alcohol were treated with HF in pyridine.Atoms other than carbon and hydrogen are labeled.

Question 9

Rank the following compounds in order of increasing oxidation level.Place the number rank (1 = lowest;4 = highest) in the blank below the structure.

Question 10

Exhibit 10-2
To answer the following question(s) consider the reaction below:

A)When propylbenzene reacts with tert-butylhypochlorite three monochlorinated products are formed in the ratios indicated.Calculate a reactivity order for each type of hydrogen atom in propylbenzene.
B)The reaction of propylbenzene with tert-butylhypochlorite proceeds by a radical substitution pathway.Draw the structure of the radical intermediate leading to each product.
C)Based on your answers to the two questions above explain why (1-chloropropyl)benzene is the major product of this reaction.

Question 11

In the discussion on relative reactivity of alkane hydrogens towards radical chlorination,we showed that the relative rate of 2° to 1° hydrogen atom abstraction is 3.5 : 1 for butane.Calculate the relative amounts of 1-chloropropane and 2-chloropropane obtained by the radical chlorination of propane,using this relative rate of reactivity.

Question 12

Predict the product of the following reaction.

Question 13

Draw: (S)-2-bromobutane

Question 14

Draw: 1,2-dichloro-1,1,2,2-tetrafluoroethane (Cryofluorane)

Question 15

Draw: 3-iodopropene

Question 16

Exhibit 10-4
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-4.Draw the resonance forms of the allylic radical intermediate that accounts for the formation of B and C.

Question 17

Exhibit 10-4
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-4.Place asterisks(*) at all allylic positions in compound A.

Question 18

Exhibit 10-2
To answer the following question(s) consider the reaction below:
Refer to Exhibit 10-2.Are any of the products of this reaction chiral? If so draw them and label the chirality center with an asterisk.

Question 19

Exhibit 10-4
Consider the reaction below to answer the following question(s).
Refer to Exhibit 10-4.D and E,below,are minor products in this reaction.Explain why.

Question 20

Exhibit 10-2
To answer the following question(s) consider the reaction below:
Refer to Exhibit 10-2.Will the product mixture of this reaction display optical activity?

Question 21

Consider the following reaction. This reaction is classified as:

A)an oxidation.
B)a reduction.
C)neither an oxidation nor a reduction.

Question 22

​Draw the mechanism of the allylic bromination of 1-cyclopentene.

Question 23

Which of the following correctly orders oxidation levels?

A)
B)
C)
D)

Question 24

Draw the mechanism of the coupling reaction between lithium diethylcopper and cis-1-chloro-1-octene.

Question 25

Which of the following is a valid comparison of organocopper and organopalladium reagents?

A)Both work equally well with alkyl compounds.
B)Palladium compounds are more toxic than copper compounds.
C)Organopalladium reactions require a larger amount of the metal.
D)Organopalladium compounds are particularly useful in from biaryl compounds.

Question 26

Draw the condensed formula for the product formed when the following substance is treated with NBS using carbon tetrachloride as the solvent.

Question 27

The following product is a simplified penicillin analog.Draw the structure of the missing reactant represented by the "?" when the reaction is carried out in the presence of a palladium catalyst.

Question 28

Consider the following reaction. This reaction is classified as:

A)an oxidation.
B)a reduction.
C)neither an oxidation nor a reduction.

Question 29

​Draw the mechanism of production of trans-3-decene from trans-1-fluoro-1-heptene.

Question 30

Which of the following is the least likely to form a Grignard reagent?

A)
B)
C)
D)
E)All will form Grignard reagents.

Question 31

Which of the following pairs are not alternative reagents to prepare the indicated products?

A)HCl,SOCl₂ - preparation of alkyl chlorides from alcohols
B)HBr,NBS - preparation of alkyl bromides from alkenes
C)Br₂ and HBr - preparation of alkyl bromides from alkanes
D)diorganocopper reagents and organopalladium compounds - forming new carbon-to-carbon bonds