Interpretation:
The reaction when hydrogen chloride reacts with 2-methyl-1,3-butadiene to form 1-chloro-3-methyl-2-butene as a major product via 1,4-addition mechanism and no product formed by 1,2-additon, is to be explained.
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 Free radical is an atom, molecule or ion that has an unpaired electron, which makes it highly chemically reactive.
舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
舧 The reaction in which there is addition of hydrogen molecule is called hydrogenation reaction.
舧
舧 Hydrogenation with platinum as a catalyst is used to convert unsaturated carbohydrates to saturated hydrocarbons
舧 Oxidation of
舧 Ozonolysis helps convert the carbon–carbon double bonds to carbon–oxygen double bond (carbonyl compounds).
舧 Dimethyl sulfide is used as a reducing agent that decomposes the intermediate formed into the carbonyl group.
舧 NBS (nitro-bromo succinimide) is a special reagent used for bromination of allylic carbocations.
舧 Bromine replaces the hydrogen attached to the carbon adjacent to the carbon bearing double bond.
舧 This method of using NBS can produce allylic bromides without bromine reacting with the double bond.
舧 Dehydration of a primary alcohol in the presence of a mineral acid like concentrated sulfuric acid results in the formation of alkene via E2 elimination.
舧 The stability of carbocation:
舧 The 1,2 – addition to a diene is the addition of an electrophile to the carbon designated as 1 and a nucleophile to the carbon designated as 2. The positions of carbons as 1 and 2 are not according to the IUPAC numbering of the molecule, but as a conjugated diene molecule. 1,4-addition results in addition of hydrogen to thee carbon designated as 1 and a halogen to the carbon designated as 4.
舧 The mechanism of 1,2 addition and 1,4-addition of hydro halogenation is given below:
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Chapter 13 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- 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
- Draw one product of an elimination reaction between the molecules below. Note: There may be several correct answers. You only need to draw one of them. You do not need to draw any of the side products of the reaction. OH + ! : ☐ + Х Click and drag to start drawing a structure.arrow_forwardFind one pertinent analytical procedure for each of following questions relating to food safety analysis. Question 1: The presence of lead, mercury and cadmium in canned tuna Question 2: Correct use of food labellingarrow_forwardFormulate TWO key questions that are are specifically in relation to food safety. In addition to this, convert these questions into a requirement for chemical analysis.arrow_forward
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