(a)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
In the Friedel-craft alkylation reaction alkyl chloride and benzene reacts to form alkylated benzene compound. The Lewis acid

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 1
The benzene ring in the presence of
Figure 2
The structure of compound formed in the given reaction is shown in Figure 2.
(b)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
In the Friedel craft alkylation reaction alkyl chloride and benzene reacts to form alkylated benzene compound. The Lewis acid

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The incomplete reaction is shown below.
The benzene reacts with chloroform to form dichloromethyl benzene. Aluminium chloride acts as catalyst in this reaction. As benzene is present in excess amount, it will again react with the dichloromethyl benzene to form triphenyl methane. The complete reaction is shown below.
Figure 3
The structure of compound formed in the given reaction is shown in Figure 3.
(c)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
In the Friedel craft alkylation reaction alkyl chloride and benzene reacts to form alkylated benzene compound. The Lewis acid

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The incomplete reaction is shown below.
Figure 4
The given compound undergoes Friedel craft alkylation reaction to form the cyclic compound. The product formed in the given reaction is
Figure 5
The structure of compound formed in the given reaction is shown in Figure 5.
(d)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
Reaction of benzene with acyl chloride in presence of Lewis acid like aluminium tricloride takes place to form acylated benzene. This reaction is known as Friedel-crafts acylation reaction. The electrophile in this reaction is a carbocation, known as acylium ion. This ion is formed when acid chloride reacts with Lewis acid.

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 6
Naphthalene reacts with
Figure 7
The structure of the product formed in the given reaction is shown in Figure 7.
(e)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
The substituted benzene ring when undergoes electrophilic substitution reaction, then it will form ortho, meta or para compounds. If the substituent present on the ring is directing the electrophile at ortho-para position, then it an ortho-para directing group. If the already present substituents direct the incoming electrophile to meta position, then it is a meta directing group. Hydroxyl group is ortho-para directing group.

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The incomplete reaction is shown below.
Figure 8
The compound
Figure 9
The structure of the product formed in the given reaction is shown in Figure 9.
(f)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
The substituted benzene ring when further undergoes electrophilic substitution reaction, and then it will form ortho, meta or para compounds. If the substituent present on the ring is directing the electrophile at ortho-para position, then it an ortho-para directing group. If the already present substituent directs the incoming electrophile to meta position then it is a meta directing group. Cyclohexyl group is ortho-para directing group.

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 10
The compound
Figure 11
The structure of the product formed in the given reaction is shown in Figure 11.
(g)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
Reaction of benzene with acyl chloride in presence of Lewis acid like aluminium tricloride to form acylated benzene is known as Friedel-crafts acylation reaction. The electrophile in the reaction is a carbocation, known as acylium ion. This ion is formed when acid chloride reacts with Lewis acid.

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 12
The compound ferrocene reacts with acyl chloride to form acylated ferrocene ring. The acetyl group is an electrophile. The electrophilic substitution reaction of ferrocene takes place to form acylated ferrocene. The
Figure 13
The structure of the product formed in the given reaction is shown in Figure 13.
(h)
Interpretation:
The structure of the product formed in the given reaction is to be shown.
Concept Introduction:
Nitration reaction takes place in the presence of nitric acid. It is an electrophilic substitution reaction. Nitronium ion is formed as electrophile in nitration reaction. The methoxy group is an activating group, it is ortho-para directing group. The nitro group is strongly deactivating group and it is meta directing group.

Answer to Problem 16.61AP
The structure of product formed in the given reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 14
The reaction of
Figure 15
The structure of the product formed in the given reaction is shown in Figure 15.
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Chapter 16 Solutions
ORGANIC CHEM +SG +SAPLING >IP<
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- How many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom moleculearrow_forwardIn the drawing area below, draw the major products of this organic reaction: 1. NaOH ? 2. CH3Br If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. No reaction. Click and drag to start drawing a structure. ☐ : A คarrow_forwardPredict the major products of the following organic reaction: NC Δ ? Some important Notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to draw bonds carefully to show important geometric relationships between substituents. Note: if your answer contains a complicated ring structure, you must use one of the molecular fragment stamps (available in the menu at right) to enter the ring structure. You can add any substituents using the pencil tool in the usual way. Click and drag to start drawing a structure. Х аarrow_forward
- Predict the major products of this organic reaction. Be sure you use dash and wedge bonds to show stereochemistry where it's important. + ☑ OH 1. TsCl, py .... 文 P 2. t-BuO K Click and drag to start drawing a structure.arrow_forwardConsider this organic reaction: ( Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. Click and drag to start drawing a structure. Х : а ค 1arrow_forwardIn the drawing area below, draw the major products of this organic reaction: If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. 1. NaH 2. CH3Br ? Click and drag to start drawing a structure. No reaction. : ☐ Narrow_forward
- + Predict the major product of the following reaction. : ☐ + ☑ ค OH H₂SO4 Click and drag to start drawing a structure.arrow_forwardConsider this organic reaction: ... OH CI Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. ☐ No Reaction. Click and drag to start drawing a structure. : аarrow_forwardConsider the following reactants: Br Would elimination take place at a significant rate between these reactants? Note for advanced students: by significant, we mean that the rate of elimination would be greater than the rate of competing substitution reactions. yes O no If you said elimination would take place, draw the major products in the upper drawing area. If you said elimination would take place, also draw the complete mechanism for one of the major products in the lower drawing area. If there is more than one major product, you may draw the mechanism that leads to any of them. Major Products:arrow_forward
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