Question and answer on the conditions for ring opening reaction and functional group conversion of cycloalkane derivatives

Ring opening reaction and functional group conversion conditions of cycloalkane derivatives
Test questions and answers
Ring opening reaction and functional group conversion conditions of cycloalkane derivatives Test questions 1. Multiple choice questions (2 points per question, 30 points in total) 1 Among the following cycloalkanes, the one that is most prone to ring opening reaction is () A. cyclohexane B. cyclopropane C. cyclobutane D. cyclopentane 2 The main products of the reaction between cyclopropane and hydrogen halides (HX) are () A. CH ∝ CH ₂ CH ₂ X B. CH ∝ CHXCH ∝ C. XCH ₂ CH ₂ D. (CH ∝) ₂ CHX 3. The main products of cyclohexene catalytic hydrogenation (using Ni as a catalyst) are () A. cyclohexane B. hexene C. hexane D. cyclohexanol 4 Cyclopentane reacts with chlorine gas under light conditions, mainly producing () A. Chlorocyclopentane B. Monochlorocyclopentane C. Polychlorocyclopentane D. Cyclopentene 5 Among the following oxidants, the one that can oxidize cyclohexanol to cyclohexanone is () A. KMnO ₄ (H ⁺) B. K ₂ Cr ₂ O ₇/H ⁺ C. Na ₂ Cr ₂ O ₇/H ₂ SO ₄ D. B (all of which can be used) 6 The main reactions of cyclohexane under concentrated sulfuric acid and high temperature conditions are () A. nitration reaction B. sulfonation reaction C. ring opening reaction D. substitution reaction 7 After reacting with ozone (O3), cyclohexene undergoes zinc powder hydrolysis, and the main products are () A. hexanal B. adipic acid C. hexanediol D. cyclohexanol 8 Among the following reagents, the one that can open the ring of cyclopropane and introduce hydroxyl groups is () A. H ₂ O/H ₂ SO ₄ B. Br ₂/CCl ₄ C. KMnO ₄/OH ⁻ (cold) D. HOCl 9. Cyclobutane undergoes ring opening reaction at high temperature, and the main products are () A. butane B. butene C. 1,3-butadiene D. 1,2-butadiene 10 1-Methylcyclohexanol is dehydrated under concentrated sulfuric acid, and the main products are () A. 1-methylcyclohexene B. 3-methylcyclohexene C. methylcyclohexane D. cyclohexyl methyl ether 11 Heating cyclohexyl bromide in NaOH/ethanol solution mainly undergoes () A. substitution reaction (hydrolysis to produce cyclohexanol) B. elimination reaction (production of cyclohexene) C. ring opening reaction D. oxidation reaction 12 Among the following reactions, which belong to the ring opening reaction of cycloalkane derivatives are () A. Nitrification of cyclohexane to produce nitrocyclohexane B. Cyclopropane reacts with H ₂ O/H ₂ SO ₄ to produce 1-propanol C. Addition of cyclohexene with bromine to produce 1,2-dibromocyclohexane D. Oxidation of cyclohexanol to produce cyclohexanone 13 Cyclopentyl toluene reacts with chlorine gas under light, mainly occurring on () A. the benzene ring B. the cyclopentane ring C. the methyl group D. the cyclopentane ring and the carbon of the methyl group Heating 1,2-dibromocyclohexane with NaOH/ethanol solution produces () A. cyclohexene B. 1,2-cyclohexanediol C. adipic acid D. hexanal 15 Which of the following statements about ring opening reactions of cycloalkane derivatives is incorrect? A. Cyclopropane and cyclobutane are prone to ring opening reactions due to their high ring tension. B. Cycloalkanes and above generally do not undergo ring opening reactions due to their low ring tension. C. Cycloalkenes can catalyze hydrogenation and ring opening reactions. D. All cyclic alkanes can undergo ring opening reactions with halogens.

2. Fill in the blank questions (1 point per blank, 20 points in total) 1 The stability of cycloalkanes is related to the size of the ring. Generally, the ____ ring is the most stable, while the ____ and ____ rings are prone to ring opening reactions due to their high ring tension. two Cyclopropane reacts with bromine at room temperature to form ____, which belongs to the ____ reaction (fill in "addition" or "substitution"). three Cyclohexanol is oxidized to ____ under the action of oxidants such as K ₂ Cr ₂ O ₇/H ₂ SO ₄. If further strongly oxidized, ____ can be generated. four Cyclohexane undergoes a ____ reaction in a mixture of concentrated nitric acid and concentrated sulfuric acid, producing ____. five Cyclopentene reacts with potassium permanganate acidic solution to open the ring and generate ____. six Cyclopropane and HBr undergo ring opening reaction in the presence of peroxide, following the ____ rule, mainly producing ____. seven Heating 1-bromocyclohexane in NaOH aqueous solution results in a ____ reaction, generating ____; Heating in NaOH ethanol solution mainly results in ____ reaction, generating ____. eight Cyclohexylene is hydrogenated under the catalysis of H ₂ and Pt, first generating ____, and further hydrogenated to open the ring to generate ____. nine Under the action of Baeyer Villiger oxidant (such as m-CPBA), cyclobutanone generates ____, which belongs to ____ rearrangement. ten Cyclohexanesulfonic acid and NaOH solution are heated together to undergo a ____ reaction, generating ____.
3、 Naming questions (2 points per question, total 10 points) 1 Write the systematic names of the following compounds:
(1) \ (\ ce {CH3-CH2-CH2-CH3} \) (cyclohexane ring has a methyl group at position 1 and an ethyl group at position 3)
(2) \ (\ ce {Br} \) (1-methylbromocyclohexane) 2 Write the structural formula of the following compound:
(1) 1,3-dimethylcyclopentane (2) 4-tert-butylcyclohexanol 4. Reaction problem (2 points per equation, 16 points in total) 1 Complete the following reaction equation (indicating the main products and reaction conditions): (1) Cyclopropane+HBr → (no peroxide) (2) Cyclohexene+KMnO ₄ (H ⁺) → (3) Cyclohexane+Cl ₂ → (light) (4) Cyclopentanol+[O] → (K ₂ Cr ₂ O ₇/H ₂ SO ₄) (5) 1,2-Dibromocyclohexane+Zn/H ₂ O → (6) Cyclohexanone+H ₂ NOH → (7) Cyclohexylchloride+NaOH (aq)/Δ → (8) Cyclohexane+concentrated H ₂ SO ₄ 24K (high temperature) → 2 Identify and correct errors in the following reaction: cyclopropane+Cl ₂ \ (\ rightarrow {light} \) ClCH ₂ CH ₂ CH ₂ Cl (Error: ____;); Correct product: ____) V. Synthesis questions (6 points per question, 12 points in total) 1 Using cyclohexane as raw material, 1,6-hexanediol (inorganic reagent optional) is synthesized.

2. Using cyclohexene as raw material, synthesize adipic acid (inorganic reagent optional). 6、 Mechanism question (12 points in total)
1. Draw the reaction mechanism of cyclopropane and HBr (without peroxide), and indicate the reaction type. (6 points)
2. Draw the reaction mechanism (E1 mechanism) for the dehydration of 1-methylcyclohexanol to 1-methylcyclohexene under the action of concentrated sulfuric acid. (6 points)
Reference answer 1. Multiple choice questions (2 points per question, 30 points in total) 1 B 2. A 3. A 4. B 5. D 6. B 7. A 8. D 9. C 10. A 11. B 12. B 13. C 14. A 15. D. 2. Fill in the blank questions (1 point per blank, 20 points in total) 1 Six yuan; Three; 4. 2 1,2-Dibromopropane; Bonus 3 Cyclohexanone; Adipic acid 4 Nitration; Nitrocyclohexane 5 Glutaric acid 6 Peroxides; 1-Bromopropane 7 Substitution (hydrolysis); Cyclohexanol; Eliminating (removing HBr); Cyclohexene 8 Cyclohexyl ethylene; N-hexane 9 Caprolactone; Baeyer Villiger 10. Substitution (hydrolysis); Sodium Cyclohexanoate III. Naming Questions (2 points per question, 10 points in total) 1 (1) 1-Methylethylcyclohexane
(2) 1-Methylbromocyclohexane 2 (1) \ (\ ce {CH3-CH (CH3) - CH2-CH2-CH2-} \) (Five membered ring with methyl group at positions 1 and 3)
(2) \ (\ ce {HO-C6H10-C (CH3) 3} \) (Cyclohexane ring with hydroxyl group at position 1 and tert butyl group at position 4) 4. Reaction problem (2 points per equation, 16 points in total) 1 (1) (2) (HOOC - (CH2) 4-COOH) (Adipic Acid) (3) \ (\ ce {C6H11Cl} \) (Chlorocyclohexane, a chlorinated product) (4) \ (\ ce {O} \) (Cyclopentanone) (5) \ (\ ce {HO-CH2-CH2-CH2-CH2-CH2-OH}) (1,6-hexanediol) (6) \ (\ ce {NOH} \) (Cyclohexanone Oxime) (7) \ (\ ce {C6H11OH} \) (Cyclohexanol) (8) (C6H11SO3H) (Cyclohexanesulfonic acid) 2 Error: Under light conditions, Cl ₂ undergoes a substitution reaction with cyclopropane (ring opening substitution); Correct product: \ (\ ce {ClCH2CH2Cl} \) (1,3-Dichloropropane, ring opening addition) V. Synthesis questions (6 points per question, 12 points in total) 1 Synthesis of 1,6-hexanediol:

\ (\ ce {cyclohexane \ nrearrow [light] {Cl2} chlorocyclohexane \ nrearrow {NaOH, H2O/Δ} cyclohexanol \ nrearrow [concentrated H2SO4] {Δ} cyclohexene)\ xrightarrow[O3]{Zn/H2O} OHC-(CH2)4-CHO \xrightarrow[NaBH4]{H2} HO-(CH2)6-OH}\)
（ 1 minute per step, correct reagents are sufficient) 2 Synthesis of Adipic Acid:
\ (\ ce {cyclohexene\ xrightarrow[O3]{Zn/H2O} OHC-(CH2)4-CHO \xrightarrow[KMnO4]{H+, Δ} HOOC-(CH2)4-COOH}\)
Or \ (\ ce {cyclohexene \ nrearrow {KMnO4/OH -, Δ} potassium adipate \ nrearrow {H+} adipic acid} \)
(3 points per step, reasonable route is sufficient) 6. Mechanism question (12 points in total) 1 Reaction mechanism between cyclopropane and HBr (electrophilic addition ring opening):
- Step 1: H ⁺ attacks cyclopropane to form a carbocation intermediate (the ternary ring is opened, and the positive charge is on the carbon with more substituents, if symmetrical, it is arbitrary);
-Step 2: Br ⁻ attacks carbocations to generate ring opening products. Reaction type: electrophilic addition ring opening reaction. (3 points for correct mechanism arrow, 2 points for correct intermediate and product, 1 point for reaction type) 2 Dehydration mechanism of 1-methylcyclohexanol (E1): - Step 1: Concentrate H ₂ SO ₄ to protonate hydroxyl groups, forming protonated alcohols; -Step 2: C-O bond breakage, forming carbocation (tertiary carbocation, more stable); -Step 3: Removal of β - H (hydrogen on adjacent carbons), formation of π - bonds in olefins, and generation of 1-methylcyclohexene (main product, following Zaitsev's rule). (2 points for each correct mechanism arrow, 1 point for correct intermediates and products)