
Concept explainers
Interpretation: The carbocation carbon that is farthest to have an octet should be identified with proper reasons.
Concept introduction: Organic compounds are covalent in nature that undergoes a reaction by heterolytic cleavage or homolytic cleavage.
In heterolytic cleavage, shared pair of electrons is taken away by one of the atoms which result in charged species. In homolytic cleavage, shared pair of electrons are equally distributed between two atom that results in free radicals.
Carbocation is a general term employed for a postively charged carbon irrespective of valency of carbon. In carbocation, carbon is bonded to 3 atoms or groups and has only sextet of electrons so it behaves as an electron-deficient species. It is
A carbocation is classified as

Explanation of Solution
Allylic and benzyl carbocations are primary carbocation but are stable due to resonance effect. In both cases the vacant
In both benzyl cation and allylic cation, delocalization occurs through resonance effect but allylic cation has 2 contributing structures whereas benzyl cation has 4 contributing structures. Greater the contributing structures greater will be stability. Therefore benzyl cation is more stable than allylic cation.
Outside box methyl carbocation, ordinary primary, secondary and tertiary carbocations are stabilized by electron releasing nature of alkyl groups. This electron releasing nature is due to inductive effect of alkyl groups. They do not exhibit any resonance.
In general, resonance effect dominates over inductive effect. The carbocations that involve delocalization through resonance effect are more stable than those where inductive effect causes stabilization.
Hence, methyl carbocation is farthest to have an octet as electron releasing nature of hydrogen is less than methyl group so is the inductive effect and it involves no resonance stabilization.
The carbocation that is farthest to have an octet is as follows:
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Chapter 8 Solutions
Organic Chemistry: A Guided Inquiry
- 111 Carbonyl Chem Choosing reagants for a Wittig reaction What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 3 1 2 2. n-BuLi • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure. × ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Usearrow_forwardA student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from the arrow. • Is the student's transformation possible? If not, check the box under the drawing area. . If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts, inorganic reagents, or other important reaction conditions above and below the arrow. • You do not need to balance the reaction, but be sure every important organic reactant or product is shown. + T X O O лет-ле HO OH HO OH This transformation can't be done in one step.arrow_forwardDetermine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X Sarrow_forward
- Predict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forward
- Determine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forwardCH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forward
- What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forwardPredict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forwardPredict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning

